1. A resist composition said composition comprising:
an acid-sensitive imaging polymer; and
a radiation-sensitive acid generator, wherein said imaging polymer comprises a silsesquioxane backbone and a solubility inhibiting pendant acid-labile moiety having a low activation energy less than about 20 kcalmol for acid catalyzed cleaving, wherein said acid-labile moiety is cleavable at room temperature and wherein at least a portion of said imaging polymer is fluorinated resist, and wherein said imaging polymer comprises a combination of monomeric units (II) and (III), (III) and (IV) or units (II) and (V), wherein the monomeric units (II) and (III) are described by the formulas:
\u2003in which
each R3 is independently selected from the group consisting of a hydrogen atom, a halogen atom, a linear alkyl, a branched alkyl, a fluorinated linear alkyl, a fluorinated branched alkyl, a fluorocycloalkyl, a fluoroaryl, or any combination thereof,
each X is independently selected from the group consisting of an oxygen atom, a sulfur atom, NR3, a linear alkyl, a branched alkyl, a fluorinated linear alkyl, a fluorinated branched alkyl, a fluorocycloalkyl, or a fluoroaryl, wherein p is an integer having the value 1 or 0,
each Y is independently selected from the group consisting of a linear alkyl, a branched alkyl, a fluorinated linear alkyl, a fluorinated branched alkyl, a fluorocycloalkyl, or a fluoroaryl, wherein q is an integer having the value 1 or 0,
each R4 is independently selected from the group consisting of a fluorine atom, a fluorinated linear alkyl, fluorinated branched alkyl, a fluorocycloalkyl, a fluoroaryl, or any combination thereof,
each R5 is independently a solubility inhibiting group, and
each R6 is independently a solubility promoting group; and
the monomeric units (IV) and (V) are described by the formulas:
2. The resist composition of claim 1, wherein said imaging polymer further comprises a pendant solubility promoting moiety.
3. The resist composition of claim 2, wherein said pendant solubility promoting moiety is selected from the group consisting of a hydroxyl, a fluoroalcohol, a carboxylic acid, an amino group, an imino group, a fluorinated imino group and a fluorinated amino group.
4. The resist composition of claim 1, wherein said solubility inhibiting pendant acid-labile moiety is selected from the group consisting of an acetal, ketal, an orthoester and fluorinated versions thereof.
5. The resist composition of claim 1, wherein at least a portion of said solubility inhibiting pendant acid-labile moiety is fluorinated.
6. The resist composition of claim 2, wherein at least a portion of said solubility promoting moiety is fluorinated.
7. The resist composition of claim 1, wherein said silsesquioxane polymer has a weight average molecular weight of about 800 to 500,000.
8. A method of forming a structure on a substrate, said method comprising:
(a) providing a substrate;
(b) applying the resist composition of claim 1 to said substrate to form a resist layer on said substrate resist;
(c) patternwise exposing said substrate to radiation, whereby acid is generated by said radiation-sensitive acid generator in exposed regions of said resist layer,
(d) removing patternwise soluble portions of said resist layer to form a pattern of spaces in said resist layer; and
(e) transferring said pattern of spaces to said substrate.
9. The method of claim 8, further comprising the step of baking the exposed resist layer to promote acid-catalyzed reaction in exposed portions of said resist layer subsequent to said step (c) of patternwise exposing.
10. The method of claim 8, wherein said polymer further comprises a pendant solubility promoting moiety.
11. The method of claim 10, wherein said pendant solubility promoting moiety is selected from the group consisting of a hydroxyl, a fluoroalcohol, a carboxylic acid, an amino group, an imino group, a fluorinated imino group and a fluorinated amino group.
12. The method of claim 8, wherein said solubility inhibiting pendant acid-labile moiety is selected from the group consisting of an acetal, a ketal, an orthoester and fluorinated versions thereof.
13. The method of claim 8, wherein said solubility inhibiting pendant acid-labile moiety is selected from the group consisting of an acetal, a ketal, an orthoester and fluorinated versions thereof.
14. The method of claim 8, wherein at least a portion of said solubility inhibiting pendant acid-labile moiety is fluorinated.
15. The method of claim 10, wherein at least a portion of said solubility promoting moiety is fluorinated.
16. The method of claim 8, wherein said silsesquioxane polymer has a weight average molecular weight of about 800 to 500,000.
17. The method of claim 8, further comprising forming a planarizing layer over said substrate, and wherein said resist layer is applied directly to said planarizing layer.
18. The method of claim 17, wherein said planarizing layer has a underlayer composition comprising:
(A) a polymer containing (i) cyclic ether moieties, (ii) saturated polycyclic moieties, and (iii) aromatic moieties if said underlayer composition does not require a separate crosslinker, or
(B) a polymer containing (i) saturated polycyclic moieties, and (ii) aromatic moieties if said underlayer composition requires a separate crosslinker.
19. The method of claim 18, wherein said underlayer composition further comprises a fluorinated polycyclic moiety, a fluorinated aromatic moiety or a combination thereof.
20. The method of claim 8, wherein said step of transferring further comprises a method selected from the group consisting of depositing, implanting and etching.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. An organic light-emitting diode, comprising:
a substrate;
a first electrode on the substrate;
a second electrode disposed opposite to the first electrode; and
an emission layer between the first electrode and the second electrode, the emission layer including an anthracene-based compound represented by Formula 1, below, and a condensed cyclic compound represented by Formula 20, below:
wherein, in Formulae 1 and 20:
n is 0 or 1;
R1 to R6 are each independently selected from a substituted or unsubstituted C1-C60 alkyl group, a 3-membered to 10-membered substituted or unsubstituted non-condensed cyclic group, and a substituted or unsubstituted condensed cyclic group with at least two condensed rings, wherein, when n is 0, at least one of R1 to R3 is a substituted or unsubstituted condensed cyclic group with at least two condensed rings, and when n is 1, at least one of R1 to R6 is a substituted or unsubstituted condensed cyclic group with at least two condensed rings;
L1, L2, Ar1, and Ar2 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C3-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C2-C60 heteroarylene group;
c and d are each independently an integer from 1 to 3;
R11, R12, R43, and R44 are each independently selected from 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C2-C60 heteroaryl group, \u2014N(Q1)(Q2), and \u2014Si(Q3)(Q4)(Q5), where Q1 to Q5 are each independently selected from a hydrogen atom, C1-C10 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group;
a and b are each independently an integer from 1 to 4;
R41 and R42 are each independently selected from 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, and a substituted or unsubstituted C2-C60 heteroaryl group;
i and j are each independently an integer from 0 to 3;
n1 is an integer from 1 to 5;
n2 is an integer from 1 to 3; and
Ar3 and Ar4 are each independently represented by one of Formulae 7A to 7F:
wherein, in Formulae 7A to 7F,
Z31 to Z44 are each independently selected from 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C2-C60 heteroaryl group, \u2014N(Q51)(Q52), and \u2014Si(Q53)(Q54)(Q55), where Q51 to Q55 are each independently selected from a hydrogen atom, a C1-C10 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group;
w1 is an integer from 1 to 4; and
w2 is an integer from 1 to 5.
2. The organic light-emitting diode as claimed in claim 1, wherein a weight ratio of the anthracene-based compound to the condensed cyclic compound in the emission layer is from about 99.9:0.01 to about 80:20.
3. The organic light-emitting diode as claimed in claim 1, wherein R1 to R6 in Formula 1 are each independently selected from:
a C1-C20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexcenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, an isothiazolyl group, an isoxazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a phenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, a biphenylenyl group, an indacenyl group, acenaphthylenyl group, a fluorenyl group, a spiro-fluorenyl group, a carbazolyl group, an anthracenyl group, a phenalenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a naphthacenyl group, a picenyl group, a pentaphenyl group, a hexacenyl group, a dibenzouranyl group, a dibenzothiophenyl group, a phenothiazinyl group, a phenoxazinyl group, a dihydrophenazinyl group, a phenoxatinyl group, and a phenanthridinyl group; and
a C1-C20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexcenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, an isothiazolyl group, an isoxazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a phenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, a biphenylenyl group, an indacenyl group, acenaphthylenyl group, a fluorenyl group, a spiro-fluorenyl group, a carbazolyl group, an anthracenyl group, a phenalenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a naphthacenyl group, a picenyl group, a pentaphenyl group, a hexacenyl group, a dibenzouranyl group, a dibenzothiophenyl group, a phenothiazinyl group, a phenoxazinyl group, a dihydrophenazinyl group, a phenoxatinyl group, and a phenanthridinyl group, each substituted with at least one 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 C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and \u2014N(Q11a)(Q12a), where Q11a and Q12a are each independently a hydrogen atom, a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group,
wherein at least one of R1 to R3 if n is 0, or at least one of R1 to R6, if n is 1, are each independently selected from:
a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, a biphenylenyl group, an indacenyl group, acenaphthylenyl group, a fluorenyl group, a spiro-fluorenyl group, a carbazolyl group, an anthracenyl group, a phenalenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a naphthacenyl group, a picenyl group, a pentaphenyl group, a hexacenyl group, a dibenzouranyl group, a dibenzothiophenyl group, a phenothiazinyl group, a phenoxazinyl group, a dihydrophenazinyl group, a phenoxatinyl group, and a phenanthridinyl group; and
a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, a biphenylenyl group, an indacenyl group, acenaphthylenyl group, a fluorenyl group, a spiro-fluorenyl group, a carbazolyl group, an anthracenyl group, a phenalenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a naphthacenyl group, a picenyl group, a pentaphenyl group, a hexacenyl group, a dibenzouranyl group, a dibenzothiophenyl group, a phenothiazinyl group, a phenoxazinyl group, a dihydrophenazinyl group, a phenoxatinyl group, and a phenanthridinyl group, each substituted with at least one 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 C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and \u2014N(Q11a)(Q12a), where Q11a and Q12a are each independently a hydrogen atom, a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group.
4. The organic light-emitting diode as claimed in claim 1, wherein R1 to R6 in Formula 1 are each independently selected from:
a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group;
a methyl group, an ethyl group, a n-propyl group, a i-propyl group, a n-butyl group, a i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, each substituted with at least one 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 C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and \u2014N(Q11a)(Q12a), where Q11a and Q12a are each independently a hydrogen atom, a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group;
groups represented by Formulae 2A to 2T below; and
group represented by Formulae 3A to 3R below,
wherein at least one of R1 to R3, if n is 0, or at least one of R1 to R6, if n is 1, are each independently selected from the groups represented by Formulae 3A to 3R below:
wherein, in Formulae 2A to 2T and Formulae 3A to 3R:
R21 to R27 are each independently selected from 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, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and \u2014N(Q11a)(Q12a), where Q11a and Q12a are each independently a hydrogen atom, a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group;
p and u are each independently an integer from 1 to 3;
q is 1 or 2;
r and x are each independently an integer from 1 to 5;
s and v are each independently an integer from 1 to 4;
t is an integer from 1 to 7;
w is an integer from 1 to 9; and
y is an integer from 1 to 6.
5. The organic light-emitting diode as claimed in claim 1, wherein R1 to R6 in Formula 1 are each independently one of:
a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, or a decyl group;
a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, or a decyl group, each substituted with at least one 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 carboxylic 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 naphthyl group, or an anthracenyl group;
a group represented by Formula 2G; or
groups represented by Formulae 4A to 4J,
wherein at least one of R1 to R3, if n is 0, or at least one of R1 to R6, if n is 1, are each independently selected from the groups represented by Formulae 4A to 4J below:
wherein, in Formula 2G, and Formulae 4A to 4J:
R21 to R25 are each independently selected from 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 carboxylic group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a dimethyl-fluorenyl group, a phenyl-carbazolyl group, a pyrenyl group, a crysenyl group, a benzothiazolyl group, a benzoxazolyl group, a phenyl-benzoimidazolyl group, and \u2014N(Q11a)(Q12a), wherein Q11a and Q12a are each independently a hydrogen atom, a C1-C10 alkyl group, a phenyl group, a naphthyl group, or an anthracenyl group;
r and x are each independently an integer from 1 to 5;
v is an integer from 1 to 4;
t is an integer from 1 to 7;
w is an integer from 1 to 9; and
y is an integer from 1 to 6.
6. The organic light-emitting diode as claimed in claim 1, wherein L1, L2, Ar1, and Ar2 in Formulae 1 and 20 are each independently selected from:
a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclooctylene group, a cyclopentenylene group, a cyclopentadienylen group, a cyclohexenylene group, a cyclohexadienylene group, a cycloheptadienylene group, a thiophenylene group, a furanylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, an isothiazolylene group, an isoxazolylene group, a thiazolylene group, an oxazolylene group, an oxadiazolylene group, a thiadiazolylene group, a triazolylene group, a phenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a biphenylenylene group, an indacenylene group, an acenaphthylenylene group, a fluorenylene group, a spiro-fluorenylene group, a carbazolylene group, an anthracenylene group, a phenalenylene group, a phenanthrenylene group, a perylenylene group, a fluoranthenylene group, a naphthacenylene group, a picenylene group, a pentaphenylene group, a hexacenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a phenothiazinylene group, a phenoxazinylene group, a dihydrophenazinylene group, a phenoxatinylene group, and a phenanthridinylene group; and
a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclooctylene group, a cyclopentenylene group, a cyclopentadienylene group, a cyclohexenylene group, a cyclohexadienylene group, a cycloheptadienylene group, a thiophenylene group, a furanylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, an isothiazolylene group, an isoxazolylene group, a thiazolylene group, an oxazolylene group, an oxadiazolylene group, a thiadiazolylene group, a triazolylene group, a phenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a biphenylenylene group, an indacenylene group, an acenaphthylenylene group, a fluorenylene group, a spiro-fluorenylene group, a carbazolylene group, an anthracenylene group, a phenalenylene group, a phenanthrenylene group, a perylenylene group, a fluoranthenylene group, a naphthacenylene group, a picenylene group, a pentaphenylene group, a hexacenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a phenothiazinylene group, a phenoxazinylene group, a dihydrophenazinylene group, a phenoxatinylene group, and a phenanthridinylene group, each substituted with at least one 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 C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and \u2014N(Q11b)(Q12b), where Q11b and Q12b are each independently a hydrogen atom, a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group.
7. The organic light-emitting diode as claimed in claim 1, wherein L1, L2, Ar1, and Ar2 in Formulae 1 and 20 are each independently selected from groups represented by Formulae 5A to 5J:
wherein R31 to R40 in Formulae 5A to 5J are each independently selected from 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, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and \u2014N(Q11b)(Q12b), where Q11b and Q12b are each independently a hydrogen atom, a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group; and
* indicates a binding site.
8. The organic light-emitting diode as claimed in claim 1, wherein, in Formula 1:
n is 1;
R1, R3, R4, and R6 are each independently a substituted or unsubstituted C1-C60 alkyl group; and
R2 and R5 are each independently selected from a 3-membered to 10-membered substituted or unsubstituted non-condensed cyclic group, and a substituted or unsubstituted condensed cyclic group with at least two condensed rings, wherein at least one of R3 and R5 is a substituted or unsubstituted condensed cyclic group with at least two condensed rings.
9. The organic light-emitting diode as claimed in claim 1, wherein, in Formula 1:
n is 0;
R1 and R3 are each independently a substituted or unsubstituted C1-C60 alkyl group; and
R2 is a substituted or unsubstituted condensed cyclic group with at least two condensed rings.
10. The organic light-emitting diode as claimed in claim 1, wherein the anthracene-based compound is one of Compounds 1 to 24 below:
11. The organic light-emitting diode as claimed in claim 1, wherein the condensed cyclic compound is a blue fluorescent dopant emitting blue light based on fluorescence mechanism.
12. The organic light-emitting diode as claimed in claim 1, wherein R41 and R42 in Formula 20 are each independently selected from:
a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group; and
a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one 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-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group.
13. The organic light-emitting diode as claimed in claim 1, wherein, in Formula 20, i=0, and j=0.
14. The organic light-emitting diode as claimed in claim 1, wherein Z31 to Z44 in Formulae 7A to 7F are each independently selected from:
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-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one 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, and a phosphoric acid group or a salt thereof;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenylene group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl 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, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a benzocarbazolyl group;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl 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, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenylene group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a benzocarbazolyl group, each substituted with at least one 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 C1-C60 alkoxy group, a C6-C60 aryl group, and a C2-C60 heteroaryl group; and
\u2014Si(Q53)(Q54)(Q55), where Q53 to Q55 are each independently selected from a hydrogen atom, a C1-C10 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group.
15. The organic light-emitting diode as claimed in claim 1, wherein Z31 to Z44 in Formulae 7A to 7F are each independently selected from:
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-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one 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, and a phosphoric acid group or a salt thereof;
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, and a benzothiophenyl group;
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, and a benzothiophenyl group, each substituted with at least one 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-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, and a triazinyl group; and
\u2014Si(Q53)(Q54)(Q55), where Q53 to Q55 are each independently selected from a hydrogen atom, a C1-C10 alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyrenyl group.
16. The organic light-emitting diode as claimed in claim 1, wherein Ar3 and Ar4 in Formula 20 are the same.
17. The organic light-emitting diode as claimed in claim 1, wherein the condensed cyclic compound represented by Formula 20 is a compound represented by Formula 20A(1), below:
18. The organic light-emitting diode as claimed in claim 1, wherein the condensed cyclic compound is one of the following Compounds 25 to 68:
19. An organic light-emitting diode, comprising:
a substrate;
a first electrode;
a second electrode disposed opposite to the first electrode; and
an emission layer between the first electrode and the second electrode, the emission layer including an anthracene-based compound represented by one of Compounds 1 to 24 below, and a condensed cyclic compound represented by one of compounds 25 to 68 below: