OPTO-ELECTRONIC DEVICE AND ELECTRONIC APPARATUS INCLUDING THE SAME
20240180029 ยท 2024-05-30
Inventors
- Youngeun CHOI (Yongin-si, KR)
- Seokgyu Yoon (Yongin-si, KR)
- Soungwook KIM (Yongin-si, KR)
- Jinsoo JUNG (Yongin-si, KR)
- Minsoo CHOI (Yongin-si, KR)
Cpc classification
H10K30/20
ELECTRICITY
International classification
Abstract
An opto-electronic device includes a first electrode, a second electrode facing the first electrode, a photoactive layer between the first electrode and the second electrode, a buffer layer between the photoactive layer and the second electrode, a first compound represented by Formula 1, a second compound represented by Formula 2, and a third compound represented by Formula 3:
##STR00001##
Claims
1. An opto-electronic device comprising: a first electrode; a second electrode facing the first electrode; a photoactive layer between the first electrode and the second electrode; a buffer layer between the photoactive layer and the second electrode; a first compound represented by Formula 1; a second compound represented by Formula 2; and a third compound represented by Formula 3: ##STR00174## wherein, in Formulae 1 to 3, X.sub.11, X.sub.21 to X.sub.24, Z.sub.21, and Z.sub.22 are each independently O, S, Se, Te, SO, SO.sub.2, C(R.sub.1)(R.sub.2), Si(R.sub.3)(R.sub.4), or N(R.sub.5), L.sub.11, L.sub.12, and L.sub.31 to L.sub.33 are each independently a single bond, a C.sub.1-C.sub.20 alkylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a11, a12, and a31 to a33 are each an integer from 1 to 3, when a11 is 2 or 3, a plurality of L.sub.11(s) are identical to or different from each other, when a12 is 2 or 3, a plurality of L.sub.12(s) are identical to or different from each other, when a31 is 2 or 3, a plurality of L.sub.31(s) are identical to or different from each other, when a32 is 2 or 3, a plurality of L.sub.32(s) are identical to or different from each other, and when a33 is 2 or 3, a plurality of L.sub.33(s) are identical to or different from each other, Ar.sub.11 to Ar.sub.13 and Ar.sub.31 to Ar.sub.33 are each independently a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, Ar.sub.12 and Ar.sub.13 are optionally linked to each other via a single bond, *O*, *S*, *C(T.sub.1)(T.sub.2)-*, *Si(T.sub.1)(T.sub.2)-*, or *N(T.sub.1)-*, Ar.sub.13 and a X.sub.11-containing 5-membered ring are optionally linked to each other via a single bond, *O*, *S*, *C(T.sub.3)(T.sub.4)-*, *Si(T.sub.3)(T.sub.4)-*, or *N(T.sub.3)-*, T.sub.1 to T.sub.4 are each independently hydrogen, deuterium, F, Cl, a cyano group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, R.sub.1 to R.sub.5, R.sub.12 to R.sub.16, and R.sub.21 to R.sub.24 are each independently hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.6 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, a C.sub.7-C.sub.60 arylalkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 heteroarylalkyl group unsubstituted or substituted with at least one R.sub.10a, C(Q.sub.1)(Q.sub.2)(Q.sub.3), Si(Q.sub.1)(Q.sub.2)(Q.sub.3), N(Q.sub.1)(Q.sub.2), B(Q.sub.1)(Q.sub.2), C(?O)(Q.sub.1), S(?O).sub.2(Q.sub.1), or P(?O)(Q.sub.1)(Q.sub.2), b12 and b13 are each an integer from 1 to 10, R.sub.10a is: deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, or a nitro group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, a C.sub.2-C.sub.60 heteroarylalkyl group, Si(Q.sub.11)(Q.sub.12)(Q.sub.13), N(Q.sub.11)(Q.sub.12), B(Q.sub.11)(Q.sub.12), C(?O)(Q.sub.11), S(?O).sub.2(Q.sub.11), P(?O)(Q.sub.11)(Q.sub.12), or any combination thereof; a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, or a C.sub.2-C.sub.60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, a C.sub.2-C.sub.60 heteroarylalkyl group, Si(Q.sub.21)(Q.sub.22)(Q.sub.23), N(Q.sub.21)(Q.sub.22), B(Q.sub.21)(Q.sub.22), C(?O)(Q.sub.21), S(?O).sub.2(Q.sub.21), P(?O)(Q.sub.21)(Q.sub.22), or any combination thereof; or Si(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), B(Q.sub.31)(Q.sub.32), C(?O)(Q.sub.31), S(?O).sub.2(Q.sub.31), or P(?O)(Q.sub.31)(Q.sub.32), Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 are each independently: hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group; or a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.7-C.sub.60 arylalkyl group, or a C.sub.2-C.sub.60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof, and and * each indicate a binding site to a neighboring atom.
2. The opto-electronic device of claim 1, wherein the photoactive layer comprises the first compound and the second compound.
3. The opto-electronic device of claim 1, wherein the buffer layer comprises the third compound.
4. The opto-electronic device of claim 1, wherein the photoactive layer comprises a first layer adjacent to the first electrode and a second layer adjacent to the buffer layer.
5. The opto-electronic device of claim 4, wherein the first layer comprises the first compound.
6. The opto-electronic device of claim 4, wherein the second layer comprises the second compound.
7. The opto-electronic device of claim 4, wherein the photoactive layer further comprises a third layer between the first layer and the second layer.
8. The opto-electronic device of claim 7, wherein the third layer comprises the first compound and the second compound.
9. The opto-electronic device of claim 1, wherein, in Formula 1, Ar.sub.11 is represented by one selected from among Formulae 1-1 to 1-3: ##STR00175## and wherein, in Formulae 1-1 to 1-3, X.sub.11a, X.sub.11b, and X.sub.11c are each independently O or S, R.sub.11a and R.sub.11b are each independently hydrogen, deuterium, F, a cyano group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.6-C.sub.60 aryl group unsubstituted or substituted with at least one R.sub.10a, b11 is an integer from 1 to 6, and indicates a binding site to a neighboring atom.
10. The opto-electronic device of claim 1, wherein, in Formula 1, Ar.sub.12 and Ar.sub.13 are each independently a benzene group or a naphthalene group.
11. The opto-electronic device of claim 1, wherein, in Formula 1, at least one selected from among L.sub.11 and L.sub.12 is a single bond.
12. The opto-electronic device of claim 1, wherein the first compound is represented by one selected from among Formulae 1A to 1E: ##STR00176## and wherein, in Formulae 1A to 1E, X.sub.11, L.sub.11, L.sub.12, Ar.sub.11 to Ar.sub.13, all, a12, R.sub.12 to R.sub.16, b12, and b13 are each the same as defined in Formula 1.
13. The opto-electronic device of claim 1, wherein, in Formula 2, Z.sub.21 and Z.sub.22 are each independently O or N(R.sub.5), and R.sub.5 is hydrogen, deuterium, F, Cl, a cyano group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.10 cycloalkyl group unsubstituted or substituted with at least one R.sub.10a, a pyrimidinyl group unsubstituted or substituted with at least one R.sub.10a, a furanyl group unsubstituted or substituted with at least one R.sub.10a, or a thiophenyl group unsubstituted or substituted with at least one R.sub.10a.
14. The opto-electronic device of claim 1, wherein, in Formula 3, Ar.sub.31 to Ar.sub.33 are each independently a benzene group unsubstituted or substituted with at least one R.sub.10a, a naphthalene group unsubstituted or substituted with at least one R.sub.10a, a fluorene group unsubstituted or substituted with at least one R.sub.10a, or a spiro-bifluorene group unsubstituted or substituted with at least one R.sub.10a.
15. The opto-electronic device of claim 1, wherein, in Formula 3, Ar.sub.31 to Ar.sub.33 are each independently represented by one selected from among Formulae 3-1 to 3-11: ##STR00177## ##STR00178## wherein, in Formulae 3-1 to 3-11, d5 is an integer from 0 to 5, d7 is an integer from 0 to 7, d8 is an integer from 0 to 8, d9 is an integer from 0 to 9, and * indicates a binding site to a neighboring atom.
16. The opto-electronic device of claim 1, wherein, in Formula 3, L.sub.31 to L.sub.33 are each independently a single bond, or are each independently represented by one selected from among Formulae 4-1 to 4-67: ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## and wherein, in Formulae 4-1 to 4-67, e3 is an integer from 0 to 3, e4 is an integer from 0 to 4, e5 is an integer from 0 to 5, e6 is an integer from 0 to 6, e7 is an integer from 0 to 7, and * and * each indicate a binding site to a neighboring atom.
17. The opto-electronic device of claim 1, wherein the first compound is at least one selected from among Compounds A1 to A108: ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209##
18. The opto-electronic device of claim 1, wherein the second compound is at least one selected from among Compounds B1 to B93: ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223##
19. The opto-electronic device of claim 1, wherein the third compound is at least one selected from among Compounds C1 to C148: ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271##
20. An electronic apparatus comprising the opto-electronic device of claim 1.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
[0029] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of the present disclosure. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain principles of the present disclosure. The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0030]
[0031]
[0032]
[0033]
[0034]
[0035]
[0036]
[0037]
[0038]
DETAILED DESCRIPTION
[0039] Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the present disclosure, and duplicative descriptions thereof may not be provided for conciseness. In this regard, the embodiments of the present disclosure may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments of the present disclosure are merely described, by referring to the drawings, to explain aspects of the present disclosure. As utilized herein, the term and/or or or may include any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression, such as, at least one of a, b, or c, at least one selected from a, b, and c, at least one selected from among a, b, and c, at least one selected from a-c, selected from a, b, and/or c, etc., indicates only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof.
[0040] One or more aspects of embodiments of the present disclosure are directed toward an opto-electronic device including: a first electrode; a second electrode facing the first electrode; a photoactive layer between the first electrode and the second electrode; a buffer layer between the photoactive layer and the second electrode; a first compound represented by Formula 1; a second compound represented by Formula 2; and a third compound represented by Formula 3:
##STR00003##
[0041] wherein, in Formulae 1 to 3,
[0042] X.sub.11, X.sub.21 to X.sub.24, Z.sub.21, and Z.sub.22 may each independently be O, S, Se, Te, SO, SO.sub.2, C(R.sub.1)(R.sub.2), Si(R.sub.3)(R.sub.4), or N(R.sub.5),
[0043] L.sub.11, L.sub.12, and L.sub.31 to L.sub.33 may each independently be a single bond, a C.sub.1-C.sub.20 alkylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0044] a11, a12, and a31 to a33 may each be an integer from 1 to 3,
[0045] when a11 is 2 or 3, a plurality of L.sub.11(s) may be identical to or different from each other, when a12 is 2 or 3, a plurality of L.sub.12(s) may be identical to or different from each other, when a31 is 2 or 3, a plurality of L.sub.31(s) may be identical to or different from each other, when a32 is 2 or 3, a plurality of L.sub.32(s) may be identical to or different from each other, and when a33 is 2 or 3, a plurality of L.sub.33(s) may be identical to or different from each other,
[0046] Ar.sub.11 to Ar.sub.13 and Ar.sub.31 to Ar.sub.33 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0047] Ar.sub.12 and Ar.sub.13 may optionally be linked to each other via a single bond, *O*, *S*, *C(T.sub.1)(T.sub.2)-*, *Si(T.sub.1)(T.sub.2)-*, or *N(T.sub.1)-*,
[0048] Ar.sub.13 and a X.sub.11-containing 5-membered ring may optionally be linked to each other via a single bond, *O*, *S*, *C(T.sub.3)(T.sub.4)-*, *Si(T.sub.3)(T.sub.4)-*, or *N(T.sub.3)-*,
[0049] T.sub.1 to T.sub.4 may each independently be hydrogen, deuterium, F, Cl, a cyano group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0050] R.sub.1 to R.sub.5, R.sub.12 to R.sub.16, and R.sub.21 to R.sub.24 may each independently be hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, a C.sub.7-C.sub.60 arylalkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 heteroarylalkyl group unsubstituted or substituted with at least one R.sub.10a, C(Q.sub.1)(Q.sub.2)(Q.sub.3), Si(Q.sub.1)(Q.sub.2)(Q.sub.3), N(Q.sub.1)(Q.sub.2), B(Q.sub.1)(Q.sub.2), C(?O)(Q.sub.1), S(?O).sub.2(Q.sub.1), or P(?O)(Q.sub.1)(Q.sub.2),
[0051] b12 and b13 may each be an integer from 1 to 10,
[0052] R.sub.10a may be:
[0053] deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, or a nitro group;
[0054] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, a C.sub.2-C.sub.60 heteroarylalkyl group, Si(Q.sub.11)(Q.sub.12)(Q.sub.13), N(Q.sub.11)(Q.sub.12), B(Q.sub.11)(Q.sub.12), C(?O)(Q.sub.11), S(?O).sub.2(Q.sub.11), P(?O)(Q.sub.11)(Q.sub.12), or any combination thereof;
[0055] a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, or a C.sub.2-C.sub.60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, a C.sub.2-C.sub.60 heteroarylalkyl group, Si(Q.sub.21)(Q.sub.22)(Q.sub.23), N(Q.sub.21)(Q.sub.22), B(Q.sub.21)(Q.sub.22), C(?O)(Q.sub.21), S(?O).sub.2(Q.sub.21), P(?O)(Q.sub.21)(Q.sub.22), or any combination thereof; or
[0056] Si(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), B(Q.sub.31)(Q.sub.32), C(?O)(Q.sub.31), S(?O).sub.2(Q.sub.31), or P(?O)(Q.sub.31)(Q.sub.32), [0057] Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 may each independently be:
[0058] hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group; or
[0059] a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.7-C.sub.60 arylalkyl group, or a C.sub.2-C.sub.60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof, and
[0060] * and * may each indicate a binding site to a neighboring atom.
[0061] The wording Ar.sub.12 and Ar.sub.13 are optionally linked to each other via a single bond, *O*, *S*, *C(T.sub.1)(T.sub.2)-*, *Si(T.sub.1)(T.sub.2)-*, or *N(T)* may refer to Formula 1A, Formula 1B, Compound A1, and/or the like described herein.
[0062] The wording Ar.sub.13 and a X.sub.11-containing 5-membered ring are optionally linked to each other via a single bond, *O*, *S*, *C(T.sub.3)(T.sub.4)-*, *Si(T.sub.3)(T.sub.4)-*, or *N(T.sub.3)-* may refer to Formula 1C, Compound A9, and/or the like described herein.
[0063] In one or more embodiments, the photoactive layer may be a single layer or a multi-layer.
[0064] In one or more embodiments, the photoactive layer may include the first compound and the second compound. For example, in some embodiments, the photoactive layer may be a single layer, and may include a mixture of the first compound and the second compound. The photoactive layer may not include (e.g., may exclude) the third compound.
[0065] In one or more embodiments, the buffer layer may be a single layer.
[0066] In one or more embodiments, the buffer layer may include the third compound. For example, in some embodiments, the buffer layer may include the third compound, and may not include (e.g., may exclude) the first compound and the second compound.
[0067] In one or more embodiments, the photoactive layer may include a first layer adjacent to the first electrode and a second layer adjacent to the buffer layer. The first layer may include the first compound. For example, in some embodiments, the first layer may not include (e.g., may exclude) the second compound. The second layer may include the second compound. For example, in some embodiments, the second layer may not include (e.g., may exclude) the first compound. For example, the first compound and the second compound may not be mixed.
[0068] In one or more embodiments, the photoactive layer may further include a third layer between the first layer and the second layer. The third layer may include the first compound and the second compound. For example, in some embodiments, the third layer may be a single layer, and may include a mixture of the first compound and the second compound.
[0069] In one or more embodiments, the opto-electronic device may further include:
[0070] a hole transport region between the first electrode and the photoactive layer, and
[0071] an electron transport region between the buffer layer and the second electrode,
[0072] the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
[0073] the electron transport region may include a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0074] In one or more embodiments, the photoactive layer may be to absorb light having a wavelength in a range of about 400 nm to about 1,000 nm. In one or more embodiments, the first compound may be to absorb light having a wavelength in a range of about 400 nm to about 1,000 nm.
[0075] In one or more embodiments, Ar.sub.11 in Formula 1 may be represented by one selected from Formulae 1-1 to 1-3:
##STR00004##
[0076] wherein, in Formulae 1-1 to 1-3,
[0077] X.sub.11a, X.sub.11b, and X.sub.11c may each independently be O or S,
[0078] R.sub.11a and R.sub.11b may each independently be hydrogen, deuterium, F, a cyano group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.6-C.sub.60 aryl group unsubstituted or substituted with at least one R.sub.10a,
[0079] b11 may be an integer from 1 to 6, and
[0080] * may indicate a binding site to a neighboring atom.
[0081] For example, in one or more embodiments, the first compound may be represented by one selected from Formula 1-1a to Formula 1-3a:
##STR00005##
[0082] In one or more embodiments, Ar.sub.12 and Ar.sub.13 in Formula 1 may each independently be a benzene group or a naphthalene group.
[0083] In one or more embodiments, at least one selected from L.sub.11 and L.sub.12 in Formula 1 may be a single bond. For example, in some embodiments, L.sub.11 and L.sub.12 may each be a single bond.
[0084] In one or more embodiments, the first compound may be represented by one selected from Formulae 1A to 1E:
##STR00006##
[0085] wherein, in Formulae 1A to 1E,
[0086] X.sub.11, L.sub.11, L.sub.12, Ar.sub.11 to Ar.sub.13, all, a12, R.sub.12 to R.sub.16, b12, and b13 may each be as defined herein.
[0087] Formulae 1A, 1B, 1 D, and 1E may be examples in which Ar.sub.12 and Ar.sub.13 are linked to each other via a single bond or *C(T.sub.1)(T.sub.2)-*.
[0088] Formulae 1C to 1E may be examples in which Ar.sub.13 and a X.sub.11-containing 5-membered ring are linked to each other via *C(T.sub.3)(T.sub.4)-*.
[0089] In one or more embodiments, in Formula 2,
[0090] Z.sub.21 and Z.sub.22 may each independently be O or N(R.sub.5), and
[0091] R.sub.5 may be hydrogen, deuterium, F, Cl, a cyano group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.10 cycloalkyl group unsubstituted or substituted with at least one R.sub.10a, a pyrimidinyl group unsubstituted or substituted with at least one R.sub.10a, a furanyl group unsubstituted or substituted with at least one R.sub.10a, or a thiophenyl group unsubstituted or substituted with at least one R.sub.10a.
[0092] For example, in one or more embodiments, in Formula 2,
[0093] Z.sub.21 and Z.sub.22 may each independently be O or N(R.sub.5), and
[0094] R.sub.5 may be: hydrogen, deuterium, F, Cl, a cyano group, or a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a; or
[0095] a group represented by one selected from among Formulae 2-1 to 2-9:
##STR00007##
[0096] wherein, in Formulae 2-1 to 2-9,
[0097] c3 may be an integer from 0 to 3,
[0098] c4 may be an integer from 0 to 4,
[0099] c5 may be an integer from 0 to 5, and
[0100] * may indicate a binding site to N.
[0101] In one or more embodiments, Z.sub.21 and Z.sub.22 in Formula 2 may be identical to each other.
[0102] In one or more embodiments, in Formula 3,
[0103] Ar.sub.31 to Ar.sub.33 may each independently be a benzene group unsubstituted or substituted with at least one R.sub.10a, a naphthalene group unsubstituted or substituted with at least one R.sub.10a, a fluorene group unsubstituted or substituted with at least one R.sub.10a, or a spiro-bifluorene group unsubstituted or substituted with at least one R.sub.10a.
[0104] For example, in some embodiments, in Formula 3,
[0105] at least one selected from Ar.sub.31 to Ar.sub.33 may be a fluorene group unsubstituted or substituted with at least one R.sub.10a or a spiro-bifluorene group unsubstituted or substituted with at least one R.sub.10a.
[0106] In one or more embodiments, in Formula 3,
[0107] Ar.sub.31 to Ar.sub.33 may each independently be represented by one selected from among Formulae 3-1 to 3-11:
##STR00008## ##STR00009##
[0108] wherein, in Formulae 3-1 to 3-11,
[0109] d5 may be an integer from 0 to 5,
[0110] d7 may be an integer from 0 to 7,
[0111] d8 may be an integer from 0 to 8,
[0112] d9 may be an integer from 0 to 9, and
[0113] * may indicate a binding site to a neighboring atom.
[0114] In one or more embodiments, in Formula 3,
[0115] L.sub.31 to L.sub.33 may each independently be a single bond, or be represented by one selected from among Formulae 4-1 to 4-67:
##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018##
[0116] wherein, in Formulae 4-1 to 4-67,
[0117] e3 may be an integer from 0 to 3,
[0118] e4 may be an integer from 0 to 4,
[0119] e5 may be an integer from 0 to 5,
[0120] e6 may be an integer from 0 to 6,
[0121] e7 may be an integer from 0 to 7, and
[0122] * and * may each indicate a binding site to a neighboring atom.
[0123] In one or more embodiments, the first compound may be at least one selected from among Compounds A1 to A108:
##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028##
[0124] In one or more embodiments, the second compound may be at least one selected from among Compounds B1 to B93:
##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041##
[0125] In one or more embodiments, the third compound may be at least one selected from among Compounds C1 to C148:
##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086##
[0126] One or more aspects of embodiments of the present disclosure are directed toward an electronic apparatus including the opto-electronic device.
[0127] In one or more embodiments, the electronic apparatus may further include: a thin-film transistor electrically connected to the first electrode; an emission layer between the first electrode and the second electrode; and a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
[0128] In one or more embodiments, the emission layer may not overlap the photoactive layer. For example, in some embodiments, the emission layer and the photoactive layer may be apart from each other on a plane.
[0129] In one or more embodiments, the opto-electronic device may include all of i) the first compound represented by Formula 1, ii) the second compound represented by Formula 2, and iii) the third compound represented by Formula 3. In some embodiments, the opto-electronic device may not i) include the second compound and the third compound without including the first compound, ii) include the first compound and the third compound without including the second compound, or iii) include the first compound and the second compound without including the third compound. As a result, the charge separation characteristics, charge transport characteristics, and/or the like of the opto-electronic device may be improved, thereby improving the external quantum efficiency of the opto-electronic device.
Description of FIGS. 1 and 2
[0130]
[0131]
[0132] In one or more embodiments, the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the opto-electronic device 30 may have a substantially single body with the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the light-emitting device 10, respectively. In one or more embodiments, the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the opto-electronic device 30 may be apart from the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the light-emitting device 10, respectively, but may include substantially the same material and be formed substantially at the same time as the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the light-emitting device 10, respectively.
[0133] Hereinafter, the structures of the opto-electronic device 30 and the light-emitting device 10 and methods of manufacturing the opto-electronic device 30 and the light-emitting device 10 will be described with reference to
First Electrode 110
[0134] In
[0135] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.
[0136] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (AlLi), calcium (Ca), magnesium-indium (MgIn), magnesium-silver (MgAg), or any combination thereof.
[0137] The first electrode 110 may have a single-layered structure including (e.g., consisting of) a single layer or a multi-layered structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
Hole Transport Region 120
[0138] The hole transport region 120 may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
[0139] The hole transport region 120 may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
[0140] For example, in one or more embodiments, the hole transport region 120 may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, the layers of each structure being sequentially stacked from the first electrode 110 in the stated order.
[0141] The hole transport region 120 may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
##STR00087##
[0142] wherein, in Formulae 201 and 202,
[0143] L.sub.201 to L.sub.204 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0144] L.sub.205 may be *O*, *S*, *N(Q.sub.201)-*, a C.sub.1-C.sub.20 alkylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.20 alkenylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0145] xa1 to xa4 may each independently be an integer from 0 to 5,
[0146] xa5 may be an integer from 1 to 10,
[0147] R.sub.201 to R.sub.204 and Q.sub.201 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0148] R.sub.201 and R.sub.202 may optionally be linked to each other via a single bond, a C.sub.1-C.sub.5 alkylene group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.2-C.sub.5 alkenylene group unsubstituted or substituted with at least one R.sub.10a, to form a C.sub.8-C.sub.60 polycyclic group (e.g., a carbazole group, etc.) unsubstituted or substituted with at least one R.sub.10a (e.g., Compound HT16, etc.),
[0149] R.sub.203 and R.sub.204 may optionally be linked to each other via a single bond, a C.sub.1-C.sub.5 alkylene group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.2-C.sub.5 alkenylene group unsubstituted or substituted with at least one R.sub.10a, to form a C.sub.8-C.sub.60 polycyclic group unsubstituted or substituted with at least one R.sub.10a, and
[0150] na1 may be an integer from 1 to 4.
[0151] For example, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY217:
##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094##
[0152] wherein, in Formulae CY201 to CY217, R.sub.10b and R.sub.10c may each be as defined herein with respect to R.sub.10a, ring CY.sub.201 to ring CY.sub.204 may each independently be a C.sub.3-C.sub.20 carbocyclic group or a C.sub.1-C.sub.20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R.sub.10a as described herein.
[0153] In one or more embodiments, ring CY.sub.2O.sub.1 to ring CY.sub.2O.sub.4 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
[0154] In one or more embodiments, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY203.
[0155] In one or more embodiments, Formula 201 may include at least one selected from groups represented by Formulae CY201 to CY203 and at least one selected from groups represented by Formulae CY204 to CY217.
[0156] In one or more embodiments, in Formula 201, xa1 may be 1, R.sub.201 may be a group represented by one selected from Formulae CY201 to CY203, xa2 may be 0, and R.sub.202 may be a group represented by one selected from Formulae CY204 to CY207.
[0157] In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one selected from Formulae CY201 to CY203.
[0158] In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one selected from Formulae CY201 to CY203, and may include at least one selected from groups represented by Formulae CY204 to CY217.
[0159] In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one selected from Formulae CY201 to CY217.
[0160] For example, in some embodiments, the hole transport region 120 may include at least one selected from among Compounds HT1 to HT46, 4,4,4-[tris(3-methylphenyl)phenylamino] triphenylamine (m-MTDATA), 4,4,4-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4,4-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), N,N-di(1-naphthalene-1-yl)-N,N-diphenylbenzidine (NPB(NPD)), ?-NPB, N,N-bis(3-methylphenyl)-N,N-diphenylbenzidine (TPD), Spiro-TPD, Spiro-NPB, methylated NPB, 4,4-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4-bis[N,N-(3-tolyl)amino]-3,3-dimethylbiphenyl (HMTPD), 4,4,4-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), and/or any combination thereof:
##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104##
[0161] A thickness of the hole transport region 120 may be in a range of about 50 ? to about 10,000 ?, for example, about 100 ? to about 4,000 ?. When the hole transport region 120 includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 ? to about 9,000 ?, for example, about 100 ? to about 1,000 ?, and a thickness of the hole transport layer may be in a range of about 50 ? to about 2,000 ?, for example, about 100 ? to about 1,500 ?. When the thicknesses of the hole transport region 120, the hole Injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
[0162] The emission auxiliary layer may be a layer that increases light-emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the emission layer 130. The electron blocking layer may be a layer that prevents or reduces leakage of electrons from the emission layer 130 to the hole transport region 120. Materials that may be included in the hole transport region 120 may be included in the emission auxiliary layer and the electron blocking layer.
p-Dopant
[0163] The hole transport region 120 may further include, in addition to the materials as described above, a charge-generation material for improving conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region 120 (e.g., in the form of a single layer including (e.g., consisting of) a charge-generation material).
[0164] The charge-generation material may be, for example, a p-dopant.
[0165] For example, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be ?3.5 eV or less.
[0166] In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing element EL1 and element EL2, or any combination thereof.
[0167] Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) (F4-TCNQ), and/or the like.
[0168] Non-limiting examples of the cyano group-containing compound may include dipyrazino[2,3-f: 2,3-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), a compound represented by Formula 221, and/or the like:
##STR00105##
[0169] wherein, in Formula 221,
[0170] R.sub.221 to R.sub.223 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, and
[0171] at least one selected from among R.sub.221 to R.sub.223 may each independently be a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each substituted with: a cyano group; F; Cl; Br; I; a C.sub.1-C.sub.20 alkyl group substituted with a cyano group, F, Cl, Br, I, or any combination thereof; or any combination thereof.
[0172] In the compound containing element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
[0173] Non-limiting examples of the metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), etc.); a lanthanide metal (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); and/or the like.
[0174] Non-limiting examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
[0175] Non-limiting examples of the non-metal may include oxygen (O), halogen (e.g., F, Cl, Br, I, etc.), and/or the like.
[0176] Non-limiting examples of the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.
[0177] Non-limiting examples of the metal oxide may include a tungsten oxide (e.g., WO, W.sub.2O.sub.3, WO.sub.2, WO.sub.3, W.sub.2O.sub.5, etc.), a vanadium oxide (e.g., VO, V.sub.2O.sub.3, VO.sub.2, V.sub.2O.sub.5, etc.), a molybdenum oxide (e.g., MoO, Mo.sub.2O.sub.3, MoO.sub.2, MoO.sub.3, Mo.sub.2O.sub.5, etc.), a rhenium oxide (e.g., ReO.sub.3, etc.), and/or the like.
[0178] Non-limiting examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, a lanthanide metal halide, and/or the like.
[0179] Non-limiting examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and/or the like.
[0180] Non-limiting examples of the alkaline earth metal halide may include BeF.sub.2, MgF.sub.2, CaF.sub.2, SrF.sub.2, BaF.sub.2, BeCl.sub.2, MgCl.sub.2, CaCl.sub.2), SrCl.sub.2, BaCl.sub.2, BeBr.sub.2, MgBr.sub.2, CaBr.sub.2, SrBr.sub.2, BaBr.sub.2, BeI.sub.2, MgI.sub.2, CaI.sub.2, SrI.sub.2, BaI.sub.2, and/or the like.
[0181] Non-limiting examples of the transition metal halide may include a titanium halide (e.g., TiF.sub.4, TiCl.sub.4, TiBr.sub.4, TiI.sub.4, etc.), a zirconium halide (e.g., ZrF.sub.4, ZrCl.sub.4, ZrBr.sub.4, ZrI.sub.4, etc.), a hafnium halide (e.g., HfF.sub.4, HfCl.sub.4, HfBr.sub.4, Hfl.sub.4, etc.), a vanadium halide (e.g., VF.sub.3, VCl.sub.3, VBr.sub.3, VI.sub.3, etc.), a niobium halide (e.g., NbF.sub.3, NbCl.sub.3, NbBr.sub.3, NbI.sub.3, etc.), a tantalum halide (e.g., TaF.sub.3, TaCl.sub.3, TaBr.sub.3, TaI.sub.3, etc.), a chromium halide (e.g., CrF.sub.3, CrCl.sub.3, CrBr.sub.3, CrI.sub.3, etc.), a molybdenum halide (e.g., MoF.sub.3, MoCl.sub.3, MoBr.sub.3, MoI.sub.3, etc.), a tungsten halide (e.g., WF.sub.3, WCl.sub.3, WBr.sub.3, WI.sub.3, etc.), a manganese halide (e.g., MnF.sub.2, MnCl.sub.2, MnBr.sub.2, MnI.sub.2, etc.), a technetium halide (e.g., TcF.sub.2, TcCl.sub.2, TcBr.sub.2, TcI.sub.2, etc.), a rhenium halide (e.g., ReF.sub.2, ReCl.sub.2, ReBr.sub.2, ReI.sub.2, etc.), an iron halide (e.g., FeF.sub.2, FeCl.sub.2, FeBr.sub.2, FeI.sub.2, etc.), a ruthenium halide (e.g., RuF.sub.2, RuCl.sub.2, RuBr.sub.2, RuI.sub.2, etc.), an osmium halide (e.g., OsF.sub.2, OsCl.sub.2, OsBr.sub.2, OsI.sub.2, etc.), a cobalt halide (e.g., CoF.sub.2, CoCl.sub.2, CoBr.sub.2, CoI.sub.2, etc.), a rhodium halide (e.g., RhF.sub.2, RhCl.sub.2, RhBr.sub.2, RhI.sub.2, etc.), an iridium halide (e.g., IrF.sub.2, IrCl.sub.2, IrBr.sub.2, IrI.sub.2, etc.), a nickel halide (e.g., NiF.sub.2, NiCl.sub.2, NiBr.sub.2, NiI.sub.2, etc.), a palladium halide (e.g., PdF.sub.2, PdCl.sub.2, PdBr.sub.2, PdI.sub.2, etc.), a platinum halide (e.g., PtF.sub.2, PtCl.sub.2, PtBr.sub.2, PtI.sub.2, etc.), a copper halide (e.g., CuF, CuCl, CuBr, CuI, etc.), a silver halide (e.g., AgF, AgCl, AgBr, AgI, etc.), a gold halide (e.g., AuF, AuCl, AuBr, AuI, etc.), and/or the like.
[0182] Non-limiting examples of the post-transition metal halide may include a zinc halide (e.g., ZnF.sub.2, ZnCl.sub.2, ZnBr.sub.2, ZnI.sub.2, etc.), an indium halide (e.g., InI.sub.3, etc.), a tin halide (e.g., SnI.sub.2, etc.), and/or the like.
[0183] Non-limiting examples of the lanthanide metal halide may include YbF, YbF.sub.2, YbF.sub.3, SmF.sub.3, YbCl, YbCl.sub.2, YbCl.sub.3, SmCl.sub.3, YbBr, YbBr.sub.2, YbBr.sub.3, SmBr.sub.3, YbI, YbI.sub.2, YbI.sub.3, SmI.sub.3, and/or the like.
[0184] Non-limiting examples of the metalloid halide may include an antimony halide (e.g., SbCl.sub.5, etc.) and/or the like.
[0185] Non-limiting examples of the metal telluride may include an alkali metal telluride (e.g., Li.sub.2Te, Na.sub.2Te, K.sub.2Te, Rb.sub.2Te, Cs.sub.2Te, etc.), an alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (e.g., TiTe.sub.2, ZrTe.sub.2, HfTe.sub.2, V.sub.2Te.sub.3, Nb.sub.2Te.sub.3, Ta.sub.2Te.sub.3, Cr.sub.2Te.sub.3, Mo.sub.2Te.sub.3, W.sub.2Te.sub.3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu.sub.2Te, CuTe, Ag.sub.2Te, AgTe, Au.sub.2Te, etc.), a post-transition metal telluride (e.g., ZnTe, etc.), a lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and/or the like.
Emission Layer 130
[0186] The light-emitting device 10 may include the emission layer 130 on the hole transport region 120.
[0187] The emission layer 130 may further include, in addition to one or more suitable organic materials, a metal-containing compound, such as an organometallic compound, an inorganic material, such as a quantum dot, and/or the like.
[0188] In one or more embodiments, the emission layer 130 may include i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer arranged between the two or more emitting units. When the emission layer 130 includes the emitting units and the charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
[0189] When the light-emitting device 10 is a full-color light-emitting device, the emission layer 130 may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a subpixel. In one or more embodiments, the emission layer 130 may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emission layer 130 may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light (e.g., combined white light).
[0190] The emission layer 130 may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0191] An amount of the dopant in the emission layer 130 may be in a range of about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0192] In one or more embodiments, the emission layer 130 may include a quantum dot.
[0193] In one or more embodiments, the emission layer 130 may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or a dopant in the emission layer 130.
[0194] A thickness of the emission layer 130 may be in a range of about 100 ? to about 1,000 ?, for example, about 200 ? to about 600 ?. When the thickness of the emission layer 130 is within these ranges, excellent or suitable luminescence characteristics may be obtained without a substantial increase in driving voltage.
Host
[0195] In one or more embodiments, the host may include a compound represented by Formula 301:
[Ar.sub.301].sub.xb11-[(L.sub.301).sub.xb1-R.sub.301].sub.xb21,Formula 301
[0196] wherein, in Formula 301,
[0197] Ar.sub.301 and L.sub.301 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0198] xb11 may be 1, 2, or 3,
[0199] xb1 may be an integer from 0 to 5,
[0200] R.sub.301 may be hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, Si(Q.sub.301)(Q.sub.302)(Q.sub.303), N(Q.sub.301)(Q.sub.302), B(Q.sub.301)(Q.sub.302), C(?O)(Q.sub.301), S(?O).sub.2(Q.sub.301), or P(?O)(Q.sub.301)(Q.sub.302),
[0201] xb21 may be an integer from 1 to 5, and
[0202] Q.sub.301 to Q.sub.303 may each be as defined herein with respect to Q.sub.1.
[0203] For example, in some embodiments, when xb11 in Formula 301 is 2 or more, two or more of Ar.sub.301(s) may be linked to each other via a single bond.
[0204] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
##STR00106##
[0205] wherein, in Formulae 301-1 and 301-2,
[0206] ring A.sub.301 to ring A.sub.304 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0207] X.sub.301 may be O, S, N[(L.sub.304).sub.xb4-R.sub.304], C(R.sub.304)(R.sub.305), or Si(R.sub.304)(R.sub.305),
[0208] xb22 and xb23 may each independently be 0, 1, or 2,
[0209] L.sub.301, xb1, and R.sub.301 may each be as defined herein,
[0210] L.sub.302 to L.sub.304 may each independently be as defined herein with respect to L.sub.301,
[0211] xb2 to xb4 may each independently be as defined herein with respect to xb1, and
[0212] R.sub.302 to R.sub.305 and R.sub.311 to R.sub.314 may each be as defined herein with respect to R.sub.301.
[0213] In one or more embodiments, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, in some embodiments, the host may include a Be complex (e.g., Compound H55), an Mg complex, a Zn complex, or any combination thereof.
[0214] In one or more embodiments, the host may include at least one selected from among Compounds H1 to H128, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4-bis(N-carbazolyl)-1,1-biphenyl (CBP), 1,3-di(carbazol-9-yl)benzene (mCP), 1,3,5-tri(carbazol-9-yl) benzene (TCP), and/or any combination thereof:
##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127##
Phosphorescent Dopant
[0215] The phosphorescent dopant may include at least one transition metal as a central metal.
[0216] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0217] In some embodiments, the phosphorescent dopant may be electrically neutral.
[0218] For example, in one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
##STR00128##
[0219] wherein, in Formulae 401 and 402,
[0220] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0221] L.sub.401 may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein, when xc1 is 2 or more, two or more of L.sub.401(s) may be identical to or different from each other,
[0222] L.sub.402 may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein, when xc2 is 2 or more, two or more of L.sub.402(s) may be identical to or different from each other,
[0223] X.sub.401 and X.sub.402 may each independently be nitrogen or carbon,
[0224] ring A.sub.401 and ring A.sub.402 may each independently be a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group,
[0225] T.sub.401 may be a single bond, *O*, *S*, *C(?O)*, *N(Q.sub.411)-*, *C(Q.sub.411)(Q.sub.412)-*, *C(Q.sub.411)=C(Q.sub.412)-*, *C(Q.sub.411)=*, or *=C?*,
[0226] X.sub.403 and X.sub.404 may each independently be a chemical bond (e.g., a covalent bond or a coordinate bond), O, S, N(Q.sub.413), B(Q.sub.413), P(Q.sub.413), C(Q.sub.413)(Q.sub.414), or Si(Q.sub.413)(Q.sub.414),
[0227] Q.sub.411 to Q.sub.414 may each be as defined herein with respect to Q.sub.1,
[0228] R.sub.401 and R.sub.402 may each independently be hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.20 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, Si(Q.sub.401)(Q.sub.402)(Q.sub.403), N(Q.sub.401)(Q.sub.402), B(Q.sub.401)(Q.sub.402), C(?O)(Q.sub.401), S(?O).sub.2(Q.sub.401), or P(?O)(Q.sub.401)(Q.sub.402),
[0229] Q.sub.401 to Q.sub.403 may each be as defined herein with respect to Q.sub.1,
[0230] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0231] * and * in Formula 402 may each indicate a binding site to M in Formula 401.
[0232] For example, in Formula 402, i) X.sub.401 may be nitrogen, and X.sub.402 may be carbon, or ii) each of X.sub.401 and X.sub.402 may be nitrogen.
[0233] In one or more embodiments, when xc1 in Formula 401 is 2 or more, two ring A.sub.401(s) in two or more of L.sub.401(s) may optionally be linked to each other via T.sub.402, which is a linking group, and/or two ring A.sub.402(s) may optionally be linked to each other via T.sub.403, which is a linking group (see Compounds PD1 to PD4 and PD7). T.sub.402 and T.sub.403 may each be as defined herein with respect to T.sub.401.
[0234] L.sub.402 in Formula 401 may be an organic ligand. For example, L.sub.402 may include a halogen, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), C(?O), an isonitrile group, a CN group, a phosphorus group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
[0235] In one or more embodiments, the phosphorescent dopant may include, for example, at least one selected from among Compounds PD1 to PD39, and/or any combination thereof:
##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134##
Fluorescent Dopant
[0236] In one or more embodiments, the fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0237] For example, in some embodiments, the fluorescent dopant may include a compound represented by Formula 501:
##STR00135##
[0238] wherein, in Formula 501,
[0239] Ar.sub.501, L.sub.501 to L.sub.503, R.sub.501, and R.sub.502 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0240] xd1 to xd3 may each independently be 0, 1, 2, or 3, and
[0241] xd4 may be 1, 2, 3, 4, 5, or 6.
[0242] For example, in some embodiments, Ar.sub.501 in Formula 501 may be a condensed cyclic group (e.g., an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed with each other.
[0243] In one or more embodiments, xd4 in Formula 501 may be 2.
[0244] For example, in some embodiments, the fluorescent dopant may include at least one selected from among Compounds FD1 to FD37, 4,4-bis(2,2-diphenylvinyl)-1,1-biphenyl (DPVBi), 4,4-bis[4-(di-phenylamino)styryl]biphenyl (DPAVBi), and/or any combination thereof:
##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140##
Delayed Fluorescence Material
[0245] In one or more embodiments, the emission layer 130 may include a delayed fluorescence material.
[0246] In the present disclosure, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescent light based on a delayed fluorescence emission mechanism.
[0247] The delayed fluorescence material included in the emission layer 130 may serve as a host or a dopant depending on the type or kind of other materials included in the emission layer 130.
[0248] In one or more embodiments, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be about 0 eV or more and about 0.5 eV or less. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.
[0249] For example, in some embodiments, the delayed fluorescence material may include i) a material including at least one electron donor (e.g., a ? electron-rich C.sub.3-C.sub.60 cyclic group, such as a carbazole group, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a ? electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group, etc.), and/or ii) a material including a C.sub.8-C.sub.60 polycyclic group in which two or more cyclic groups are condensed together while sharing boron (B).
[0250] Non-limiting examples of the delayed fluorescence material may include at least one selected from among Compounds DF1 to DF14:
##STR00141## ##STR00142## ##STR00143## ##STR00144##
Quantum Dot
[0251] In one or more embodiments, the emission layer 130 may include a quantum dot.
[0252] The term quantum dot as utilized herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of one or more suitable emission wavelengths according to the size of the crystal.
[0253] A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
[0254] The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
[0255] The wet chemical process is a method including mixing a precursor material with an organic solvent and then growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled or selected through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0256] The quantum dot may include a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, a Group IV element or compound, or any combination thereof.
[0257] Non-limiting examples of the Group II-VI semiconductor compound may include: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.
[0258] Non-limiting examples of the Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. In one or more embodiments, the Group III-V semiconductor compound may further include a Group II element. Non-limiting examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and/or the like.
[0259] Non-limiting examples of the Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga.sub.2Se.sub.3, GaTe, InS, InSe, In.sub.2S.sub.3, In.sub.2Se.sub.3, or InTe; a ternary compound, such as InGaS.sub.3 or InGaSe.sub.3; or any combination thereof.
[0260] Non-limiting examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS.sub.2, CuInS, CuInS.sub.2, CuGaO.sub.2, AgGaO.sub.2, or AgAlO.sub.2; a quaternary compound, such as AgInGaS or AgInGaS.sub.2; or any combination thereof.
[0261] Non-limiting examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.
[0262] The Group IV element or compound may include: a single element, such as Si or Ge; a binary compound, such as SiC or SiGe; or any combination thereof.
[0263] Each element included in a multi-element compound, such as the binary compound, the ternary compound, and the quaternary compound, may be present at a substantially uniform concentration or non-substantially uniform concentration in a particle.
[0264] In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or a core-shell dual structure. For example, in some embodiments, a material included in the core and a material included in the shell may be different from each other.
[0265] The shell of the quantum dot may act as a protective layer that prevents chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. An interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the core.
[0266] Non-limiting examples of the shell of the quantum dot may include an oxide of metal, metalloid, or non-metal, a semiconductor compound, or any combination thereof. Non-limiting examples of the oxide of metal, metalloid, or non-metal may include: a binary compound, such as SiO.sub.2, Al.sub.2O.sub.3, TiO.sub.2, ZnO, MnO, Mn.sub.2O.sub.3, Mn.sub.3O.sub.4, CuO, FeO, Fe.sub.2O.sub.3, Fe.sub.3O.sub.4, CoO, Co.sub.3O.sub.4, or NiO; a ternary compound, such as MgAl.sub.2O.sub.4, CoFe.sub.2O.sub.4, NiFe.sub.2O.sub.4, or CoMn.sub.2O.sub.4; or any combination thereof. Non-limiting examples of the semiconductor compound may include, as described herein, a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, or any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0267] A full width at half maximum (FWHM) of an emission spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less, and within these ranges, color purity or color reproducibility may be improved. In some embodiments, because the light emitted through the quantum dot is emitted in all directions, the viewing angle of light may be improved.
[0268] In some embodiments, the quantum dot may be in the form of a substantially spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.
[0269] Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands may be obtained from an emission layer including the quantum dot. Accordingly, by utilizing quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths may be implemented. In one or more embodiments, the size of the quantum dot may be selected to emit red, green and/or blue light. In some embodiments, the size of the quantum dot may be configured to emit white light by combining light of one or more suitable colors.
Photoactive Layer 135
[0270] The opto-electronic device 30 may include the photoactive layer 135 on the hole transport region 120. The photoactive layer 135 may be between the hole transport region 120 and the buffer layer 137. In one or more embodiments, the photoactive layer 135 may be arranged between the hole transport layer included in the hole transport region 120 and the buffer layer 137. In one or more embodiments, the photoactive layer 135 may be arranged between the emission auxiliary layer included in the hole transport region 120 and the buffer layer 137.
[0271] The photoactive layer 135 may include the first compound and the second compound. In one or more embodiments, the first compound and the second compound may be mixed to be included in the photoactive layer 135. For example, in some embodiments, the photoactive layer 135 may be a single layer including the first compound and the second compound.
[0272] The photoactive layer 135 may be to absorb light incident to the electronic apparatus to form excitons. The excitons may generate holes and electrons. For example, the photoactive layer 135 may be to absorb light to generate an electrical signal. In detail, the first compound included in the photoactive layer 135 may serve as a donor for supplying electrons, and the second compound included in the photoactive layer 135 may serve as an acceptor for receiving electrons. Accordingly, the opto-electronic device 30 including the photoactive layer 135 may serve as a photosensor. For example, in some embodiments, the opto-electronic device 30 may serve as a fingerprint recognition sensor, which will be described with reference to
Buffer Layer 137
[0273] The opto-electronic device 30 may include the buffer layer 137 on the photoactive layer 135. The buffer layer 137 may be between the electron transport region 140 and the photoactive layer 135.
[0274] The buffer layer 137 may include the third compound. For example, in some embodiments, the buffer layer 137 may not include (e.g., may exclude) the first compound and the second compound.
[0275] The buffer layer 137 may control injection of electrons, and may prevent or reduce leakage of holes.
Electron Transport Region 140
[0276] The electron transport region 140 may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
[0277] The electron transport region 140 may include a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0278] For example, the electron transport region 140 may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, or an electron control layer/electron transport layer/electron injection layer structure, the layers of each structure being sequentially stacked from the emission layer 130 in the stated order.
[0279] In one or more embodiments, the electron transport region 140 (e.g., the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region 140) may include a metal-free compound including at least one ? electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group.
[0280] For example, in some embodiments, the electron transport region 140 may include a compound represented by Formula 601:
[Ar.sub.601].sub.xe11-[(L.sub.601).sub.xe1-R.sub.601].sub.xe21,Formula 601
[0281] wherein, in Formula 601,
[0282] Ar.sub.601 and L.sub.601 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0283] xe11 may be 1, 2, or 3,
[0284] xe1 may be 0, 1, 2, 3, 4, or 5,
[0285] R.sub.601 may be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, Si(Q.sub.601)(Q.sub.602)(Q.sub.603), C(?O)(Q.sub.601), S(?O).sub.2(Q.sub.601), or P(?O)(Q.sub.601)(Q.sub.602),
[0286] Q.sub.601 to Q.sub.603 may each be as defined herein with respect to Q.sub.1,
[0287] xe21 may be 1, 2, 3, 4, or 5, and
[0288] at least one selected from among Ar.sub.601, L.sub.601, and R.sub.601 may each independently be a ? electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group unsubstituted or substituted with at least one R.sub.10a.
[0289] For example, in some embodiments, when xe11 in Formula 601 is 2 or more, two or more of Ar.sub.601(s) may be linked to each other via a single bond.
[0290] In one or more embodiments, Ar.sub.601 in Formula 601 may be a substituted or unsubstituted anthracene group.
[0291] In one or more embodiments, the electron transport region 140 may include a compound represented by Formula 601-1:
##STR00145##
[0292] wherein, in Formula 601-1,
[0293] X.sub.614 may be N or C(R.sub.614), X.sub.615 may be N or C(R.sub.615), X.sub.616 may be N or C(R.sub.616), and at least one selected from among X.sub.614 to X.sub.616 may be N,
[0294] L.sub.611 to L.sub.613 may each be as defined herein with respect to L.sub.601,
[0295] xe611 to xe613 may each be as defined herein with respect to xe1,
[0296] R.sub.611 to R.sub.613 may each be as defined herein with respect to R.sub.601, and
[0297] R.sub.614 to R.sub.616 may each independently be hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a.
[0298] For example, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
[0299] The electron transport region 140 may include at least one selected from among Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinolinato)aluminum (Alq.sub.3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1-biphenyl-4-olato)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), and/or any combination thereof:
##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161##
[0300] A thickness of the electron transport region 140 may be from about 100 ? to about 5,000 ?, for example, about 160 ? to about 4,000 ?. When the electron transport region 140 includes a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the hole blocking layer or the electron control layer may each independently be in a range of about 20 ? to about 1,000 ?, for example, about 30 ? to about 300 ?, and a thickness of the electron transport layer may be in a range of about 100 ? to about 1,000 ?, for example, about 150 ? to about 500 ?. When the thicknesses of the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region 140 are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
[0301] In one or more embodiments, the electron transport region 140 (e.g., the electron transport layer in the electron transport region 140) may further include, in addition to the materials described above, a metal-containing material.
[0302] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0303] For example, in some embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
##STR00162##
[0304] In one or more embodiments, the electron transport region 140 may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
[0305] The electron injection layer may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
[0306] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0307] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0308] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0309] The alkali metal-containing compound may include an alkali metal oxide, such as Li.sub.2O, Cs.sub.2O, or K.sub.2O, an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, Ba.sub.xSr.sub.1-xO (wherein x is a real number satisfying the condition of 0<x<1), or Ba.sub.xCa.sub.1-xO (wherein x is a real number satisfying the condition of 0<x<1). The rare earth metal-containing compound may include YbF.sub.3, ScF.sub.3, Sc.sub.2O.sub.3, Y.sub.2O.sub.3, Ce.sub.2O.sub.3, GdF.sub.3, TbF.sub.3, YbI.sub.3, ScI.sub.3, TbI.sub.3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Non-limiting examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La.sub.2Te.sub.3, Ce.sub.2Te.sub.3, Pr.sub.2Te.sub.3, Nd.sub.2Te.sub.3, Pm.sub.2Te.sub.3, Sm.sub.2Te.sub.3, Eu.sub.2Te.sub.3, Gd.sub.2Te.sub.3, Tb.sub.2Te.sub.3, Dy.sub.2Te.sub.3, Ho.sub.2Te.sub.3, Er.sub.2Te.sub.3, Tm.sub.2Te.sub.3, Yb.sub.2Te.sub.3, Lu.sub.2Te.sub.3, and/or the like.
[0310] The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively, and ii) a ligand linked to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0311] In one or more embodiments, the electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0312] In one or more embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, in some embodiments, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
[0313] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0314] A thickness of the electron injection layer may be in a range of about 1 ? to about 100 ?, for example, about 3 ? to about 90 ?. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
Second Electrode 150
[0315] The second electrode 150 may be on the electron transport region 140. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function, may be utilized.
[0316] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (A1-Li), calcium (Ca), magnesium-indium (MgIn), magnesium-silver (MgAg), ytterbium (Yb), silver-ytterbium (AgYb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0317] The second electrode 150 may have a single-layered structure or a multi-layered structure including a plurality of layers.
Capping Layer
[0318] In one or more embodiments, a first capping layer may be arranged outside the first electrode 110, and/or a second capping layer may be arranged outside the second electrode 150. In some embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the emission layer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the emission layer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the emission layer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
[0319] Light generated in the emission layer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer, or light generated in the emission layer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
[0320] The first capping layer and the second capping layer may increase external luminescence efficiency according to the principle of constructive interference. Consequently, the light extraction efficiency of the light-emitting device 10 may be increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
[0321] Each of the first capping layer and the second capping layer may include a material having a refractive index of about 1.6 or more (at 589 nm).
[0322] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0323] At least one selected from among the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include an amine group-containing compound.
[0324] For example, in some embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0325] In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include at least one selected from among Compounds HT28 to HT33, at least one selected from among Compounds CP1 to CP6, ?-NPB, or any combination thereof:
##STR00163##
Film
[0326] In one or more embodiments, the electronic apparatus may further include a film. The film may be, for example, an optical member (or a light control member) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency improvement layer, a selective light absorption layer, a polarizing layer, a quantum dot-containing layer, etc.), a light blocking member (e.g., a light reflection layer, a light absorption layer, etc.), a protection member (e.g., an insulating layer, a dielectric layer, etc.), and/or the like.
Description For FIG. 3
[0327]
[0328] The opto-electronic device 31 shown in
[0329] The opto-electronic device 31 may include the photoactive layer 135 between the hole transport region 120 and the buffer layer 137. In one or more embodiments, the photoactive layer 135 may be between the hole transport layer included in the hole transport region 120 and the buffer layer 137. In one or more embodiments, the photoactive layer 135 may be between the emission auxiliary layer included in the hole transport region 120 and the buffer layer 137.
[0330] In one or more embodiments, the photoactive layer 135 may include a first layer 131 adjacent to the hole transport region 120 and a second layer 132 adjacent to the buffer layer 137. In one or more embodiments, the first layer 131 may be in direct contact with the second layer 132.
[0331] In one or more embodiments, the first layer 131 may be in direct contact with the hole transport layer included in the hole transport region 120. In one or more embodiments, the first layer 131 may be in direct contact with the emission auxiliary layer arranged on the hole transport layer.
[0332] In one or more embodiments, the second layer 132 may be in direct contact with the buffer layer 137.
[0333] The first layer 131 may include the first compound. For example, the first layer 131 may not include (e.g., may exclude) the second compound.
[0334] The second layer 132 may include the second compound. For example, the second layer 132 may not include (e.g., may exclude) the first compound.
[0335] For example, the photoactive layer 135 may have a multi-layered structure divided into the first layer 131 including the first compound and the second layer 132 including the second compound.
[0336] The photoactive layer 135 may be to absorb incident light to form excitons. The excitons may generate holes and electrons. For example, the photoactive layer 135 may be to absorb light to generate an electrical signal. In detail, the first compound included in the first layer 131 may serve as a donor for supplying electrons, and the second compound included in the second layer 132 may serve as an acceptor for receiving electrons. Accordingly, the opto-electronic device 31 including the photoactive layer 135 may serve as a photosensor. For example, in one or more embodiments, the opto-electronic device 31 may serve as a fingerprint recognition sensor, which will be described with reference to
Description of FIG. 4
[0337]
[0338] The opto-electronic device 32 shown in
[0339] The opto-electronic device 32 may include the photoactive layer 135 between the hole transport region 120 and the buffer layer 137. In one or more embodiments, the photoactive layer 135 may be between the hole transport layer included in the hole transport region 120 and the buffer layer 137. In one or more embodiments, the photoactive layer 135 may be between the emission auxiliary layer included in the hole transport region 120 and the buffer layer 137.
[0340] The photoactive layer 135 may include the first layer 131 adjacent to the hole transport region 120, the second layer 132 adjacent to the buffer layer 137, and a third layer 133 between the first layer 131 and the second layer 132. In one or more embodiments, the third layer 133 may be in direct contact with the first layer 131 and/or the second layer 132.
[0341] In one or more embodiments, the first layer 131 may be in direct contact with the hole transport layer included in the hole transport region 120. In one or more embodiments, the first layer 131 may be in direct contact with the emission auxiliary layer arranged on the hole transport layer.
[0342] In one or more embodiments, the second layer 132 may be in direct contact with the buffer layer 137.
[0343] The first layer 131 may include the first compound. For example, the first layer 131 may not include (e.g., may exclude) the second compound.
[0344] The second layer 132 may include the second compound. For example, the second layer 132 may not include (e.g., may exclude) the first compound.
[0345] The third layer 133 may include the first compound and the second compound. For example, the first compound and the second compound may be mixed to be included in the third layer 133.
[0346] For example, in some embodiments, the photoactive layer 135 may have a multi-layered structure divided into the first layer 131 including the first compound, the third layer 133 including both (e.g., simultaneously) the first compound and the second compound, and the second layer 132 including the second compound.
[0347] The photoactive layer 135 may be to absorb incident light to form excitons. The excitons may generate holes and electrons. For example, the photoactive layer 135 may be to absorb light to generate an electrical signal. In detail, the first compound included in each of the first layer 131 and the third layer 133 may serve as a donor for supplying electrons, and the second compound included in each of the second layer 132 and the third layer 133 may serve as an acceptor for receiving electrons. Accordingly, the opto-electronic device 32 including the photoactive layer 135 may serve as a photosensor. For example, in some embodiments, the opto-electronic device 32 may serve as a fingerprint recognition sensor, which will be described with reference to
Electronic Apparatus
[0348] The light-emitting device 10 and the opto-electronic device 30, 31, or 32 may be included in one or more suitable electronic apparatuses. For example, the electronic apparatus may be a light-emitting apparatus, an authentication apparatus, and/or the like.
[0349] The electronic apparatus (e.g., a light-emitting apparatus) may further include, in addition to the light-emitting device 10 and the opto-electronic device 30, 31, or 32, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one direction in which light emitted from the light-emitting device 10 travels. For example, in some embodiments, the light emitted from the light-emitting device 10 may be blue light or white light (e.g., combined white light). Details on the light-emitting device 10 may be as described above. In one or more embodiments, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a quantum dot as described herein.
[0350] The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
[0351] A pixel defining layer may be arranged among the subpixel areas to define each of the subpixel areas.
[0352] The color filter may further include a plurality of color filter areas and light-shielding patterns arranged among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns arranged among the color conversion areas.
[0353] The color filter areas (or the color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. For example, in some embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, in one or mor embodiments, the color filter areas (or the color conversion areas) may include quantum dots. In some embodiments, the first area may include a red quantum dot to emit red light, the second area may include a green quantum dot to emit green light, and the third area may not include (e.g., may exclude) a quantum dot. Details on the quantum dot may be as described herein. The first area, the second area, and/or the third area may each further include a scatterer.
[0354] For example, in one or more embodiments, the light-emitting device 10 may be to emit first light, the first area may be to absorb the first light to emit first-first color light, the second area may be to absorb the first light to emit second-first color light, and the third area may be to absorb the first light to emit third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In some embodiments, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0355] In one or more embodiments, the electronic apparatus may further include a thin-film transistor, in addition to the opto-electronic device 30, 31, or 32 and the light-emitting device 10 as described above. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, and one selected from among the source electrode and the drain electrode may be electrically connected to the first electrode 110 or the second electrode 150 of the light-emitting device 10.
[0356] The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
[0357] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.
[0358] The electronic apparatus may further include a sealing portion for sealing the light-emitting device 10. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-emitting device 10. The sealing portion may allow light from the light-emitting device 10 to be extracted to the outside, and may concurrently (e.g., simultaneously) prevent or reduce ambient air and moisture from penetrating into the light-emitting device 10. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.
[0359] Various functional layers may be additionally arranged on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the utilization of the electronic apparatus. Non-limiting examples of the functional layer may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (e.g., fingertips, pupils, etc.).
[0360] The authentication apparatus may further include, in addition to the opto-electronic device 30, 31, or 32 and the light-emitting device 10 as described above, a biometric information collector.
[0361] The electronic apparatus may be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
Electronic Device
[0362] The opto-electronic device 30, 31, or 32 may be included in one or more suitable electronic devices.
[0363] For example, the electronic device including the opto-electronic device 30, 31, or 32 may be at least one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and/or signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual or augmented-reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.
[0364] Because the opto-electronic device 30, 31, or 32 has excellent or suitable photoelectric characteristics, the electronic device including the opto-electronic device 30, 31, or 32 may serve as an optical sensor, such as a fingerprint recognition sensor.
Description of FIGS. 5 and 6
[0365]
[0366] The electronic apparatus of
[0367] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A barrier layer 210 may be arranged on the substrate 100. The barrier layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
[0368] The thin-film transistor TFT may be arranged on the barrier layer 210. The thin-film transistor TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0369] The active layer 220 may include an inorganic semiconductor, such as silicon or polysilicon, an organic semiconductor, and/or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0370] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be arranged on the active layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.
[0371] An interlayer insulating film 250 may be arranged on the gate electrode 240. The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
[0372] The source electrode 260 and the drain electrode 270 may be arranged on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be in contact with the exposed portions of the source region and the drain region of the active layer 220, respectively.
[0373] The light-emitting device 10 and the opto-electronic device 30 may be arranged on the thin-film transistor TFT.
[0374] The thin-film transistor TFT electrically connected to the light-emitting device 10 may be to transmit an electrical signal for driving the light-emitting device 10. The thin-film transistor TFT electrically connected to the opto-electronic device 30 may be to transmit an electrical signal generated by the opto-electronic device 30. The thin-film transistor TFT may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device 10 and the opto-electronic device 30 may be provided on the passivation layer 280.
[0375] The light-emitting device 10 may include a first electrode 110, a hole transport region 120, an emission layer 130, an electron transport region 140, and a second electrode 150. The light-emitting device 10 may further include a buffer layer 137 arranged between the emission layer 130 and the electron transport region 140. The opto-electronic device 30 may include a first electrode 110, a hole transport region 120, a photoactive layer 135, a buffer layer 137, an electron transport region 140, and a second electrode 150.
[0376] The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may expose certain regions of the source electrode 260 and the drain electrode 270 without completely covering the source electrode 260 and the drain electrode 270, and the first electrode 110 may be connected to the exposed regions of the source electrode 260 or the drain electrode 270.
[0377] A pixel defining layer 290 including an insulating material may be arranged on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film.
[0378] The hole transport region 120 may be arranged on the pixel defining layer 290. The hole transport region 120 included in the light-emitting device 10 and the hole transport region 120 included in the opto-electronic device 30 may be integrally formed as a single body. The hole transport region 120 included in the light-emitting device 10 and the hole transport region 120 included in the opto-electronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed substantially at the same time.
[0379] Each of the emission layer 130 and the photoactive layer 135 may be arranged on the hole transport region 120. Each of the emission layer 130 and the photoactive layer 135 may overlap the certain region of the corresponding first electrode 110 that is exposed by the pixel defining layer 290.
[0380] The buffer layer 137 may be arranged on the photoactive layer 135. In some embodiments, when the light-emitting device 10 includes the buffer layer 137, the buffer layer 137 included in the opto-electronic device 30 may extend to be arranged on the emission layer 130. In these embodiments, the buffer layer 137 included in the light-emitting device 10 and the buffer layer 137 included in the opto-electronic device 30 may be integrally formed as a single body. The buffer layer 137 included in the light-emitting device 10 and the buffer layer 137 included in the opto-electronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed substantially at the same time.
[0381] The electron transport region 140 may be arranged on the emission layer 130 and the photoactive layer 135. The electron transport region 140 included in the light-emitting device 10 and the electron transport region 140 included in the opto-electronic device 30 may be integrally formed as a single body. The electron transport region 140 included in the light-emitting device 10 and the electron transport region 140 included in the opto-electronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed substantially at the same time.
[0382] The second electrode 150 may be arranged on the electron transport region 140. The second electrode 150 included in the light-emitting device 10 and the second electrode 150 included in the opto-electronic device 30 may be integrally formed as a single body. The second electrode 150 included in the light-emitting device 10 and the second electrode 150 included in the opto-electronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed substantially at the same time.
[0383] A capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0384] The encapsulation portion 300 may be arranged on the capping layer 170. The encapsulation portion 300 may be arranged on the light-emitting device 10 and the opto-electronic device 30 to protect the light-emitting device 10 and the opto-electronic device 30 from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiN.sub.x), silicon oxide (SiO.sub.x), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or a combination of the inorganic film and the organic film.
[0385] The light-emitting device 10 may be to emit lights L1, L2, and L3. For example, the lights L1, L2, and L3 may each be green light.
[0386] The light L3 of the lights L1, L2, and L3 that have been emitted may be incident on an object 600 outside the electronic apparatus. For example, the object 600 may be a finger of a user of the electronic apparatus. A light L3 reflected by the object 600 may be incident on the opto-electronic device 30.
[0387] The photoactive layer 135 may be to absorb the incident light L3 to form excitons. The excitons may generate holes and electrons. For example, the photoactive layer 135 may be to absorb light to generate an electrical signal. In detail, the first compound included in the photoactive layer 135 may serve as a donor for supplying electrons, and the second compound included in the photoactive layer 135 may serve as an acceptor for receiving electrons. For example, the opto-electronic device 30 may detect energy of the light L3 and convert the detected energy into an electrical signal. Accordingly, the opto-electronic device 30 may recognize the object 600 that has come into contact with (or approached) the electronic apparatus. Accordingly, the opto-electronic device 30 including the photoactive layer 135 may serve as an optical sensor (e.g., a fingerprint recognition sensor).
[0388]
[0389] The electronic apparatus of
Description of FIG. 7
[0390]
[0391] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The electronic device 1 may implement an image through an array of a plurality of pixels that are two-dimensionally arranged in the display area DA.
[0392] The non-display area NDA is an area in which an image is not displayed, and may entirely surround the display area DA. A driver for providing an electrical signal or power to a light-emitting device arranged in the display area DA may be arranged in the non-display area NDA. A pad, which is an area to which an electronic element or a printed circuit board may be electrically connected, may be arranged in the non-display area NDA.
[0393] The electronic device 1 may have different lengths in the x-axis direction and in the y-axis direction. For example, in one or more embodiments, as shown in
Description of FIGS. 8 and 9A to 9C
[0394]
[0395] Referring to
[0396] In one or more embodiments, the vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a certain direction according to rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover apparatus, a bicycle, or a train running on a track.
[0397] The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical apparatuses necessary for driving are installed as the remaining parts except for the body. The exterior of the body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, and a pillar provided at a boundary between doors. The chassis of the vehicle 1000 may include a power generating apparatus, a power transmitting apparatus, a driving apparatus, a steering apparatus, a braking apparatus, a suspension apparatus, a transmission apparatus, a fuel apparatus, front and rear wheels, left and right wheels, and/or the like.
[0398] The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display apparatus 2.
[0399] The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
[0400] The side window glass 1100 may be installed on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
[0401] In one or more embodiments, the side window glasses 1100 may be apart from each other in the x-direction or the ?x-direction. For example, the first side window glass 1110 and the second side window glass 1120 may be apart from each other in the x direction or the ?x direction. In other words, an imaginary straight line L connecting the side window glasses 1100 to each other may extend in the x direction or the ?x direction. For example, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the ?x direction.
[0402] The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
[0403] The side mirror 1300 may provide a view of the rear of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the body. In one or more embodiments, a plurality of side mirrors 1300 may be provided. One of the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. Another one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.
[0404] The cluster 1400 may be arranged in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a hodometer, an automatic transmission selection lever indicator, a door open warning light, an engine oil warning light, and/or a low fuel warning light.
[0405] The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio apparatus, an air conditioning apparatus, and/or a heater of a seat are arranged. The center fascia 1500 may be arranged on one side of the cluster 1400.
[0406] The passenger seat dashboard 1600 may be apart from the cluster 1400 with the center fascia 1500 therebetween. In one or more embodiments, the cluster 1400 may be arranged to correspond to a driver seat, and the passenger seat dashboard 1600 may be arranged to correspond to a passenger seat. In one or more embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
[0407] In one or more embodiments, the display apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In some embodiments, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be arranged on at least one selected from among the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
[0408] The display apparatus 2 may include an organic light-emitting display apparatus, an inorganic electroluminescent (EL) display apparatus, a quantum dot display apparatus, and/or the like. Hereinafter, an organic light-emitting display apparatus including the opto-electronic device and the light-emitting device according to one or more embodiments of the present disclosure will be described as an example, but one or more suitable types (kinds) of display apparatuses as described above may be utilized in embodiments of the present disclosure.
[0409] Referring to
[0410] Referring to
[0411] Referring to
Manufacturing Method
[0412] Respective layers included in the hole transport region 120, the emission layer 130, the photoactive layer 135, and respective layers included in the electron transport region 140 may be formed in a certain region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and/or the like.
[0413] When respective layers included in the hole transport region 120, the emission layer 130, the photoactive layer 135, and respective layers included in the electron transport region 140 are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100? C. to about 500? C., a vacuum degree of about 10.sup.?8 torr to about 10.sup.?3 torr, and a deposition speed of about 0.01 ?/sec to about 100 ?/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
Definition of Terms
[0414] The term C.sub.3-C.sub.60 carbocyclic group as utilized herein refers to a cyclic group that has 3 to 60 carbon atoms and includes (e.g., consists of) only carbon atoms as ring-forming atoms. The term C.sub.1-C.sub.60 heterocyclic group as utilized herein refers to a cyclic group that has 1 to 60 carbon atoms and further includes, in addition to carbon atoms, a heteroatom as a ring-forming atom. The C.sub.3-C.sub.60 carbocyclic group and the C.sub.1-C.sub.60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the C.sub.1-C.sub.60 heterocyclic group may have 3 to 61 ring-forming atoms.
[0415] The term cyclic group as utilized herein may include both (e.g., simultaneously) the C.sub.3-C.sub.60 carbocyclic group and the C.sub.1-C.sub.60 heterocyclic group.
[0416] The term ? electron-rich C.sub.3-C.sub.60 cyclic group as utilized herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *N?* as a ring-forming moiety.
[0417] The term ? electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group as utilized herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *N?* as a ring-forming moiety.
[0418] For example,
[0419] the C.sub.3-C.sub.60 carbocyclic group may be i) a group T1 or ii) a condensed cyclic group in which two or more groups T1 are condensed with each other (e.g., a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),
[0420] the C.sub.1-C.sub.60 heterocyclic group may be i) a group T2, ii) a condensed cyclic group in which two or more groups T2 are condensed with each other, or iii) a condensed cyclic group in which at least one group T2 and at least one group T1 are condensed with each other (e.g., a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
[0421] the ? electron-rich C.sub.3-C.sub.60 cyclic group may be i) a group T1, ii) a condensed cyclic group in which two or more groups T1 are condensed with each other, iii) a group T3, iv) a condensed cyclic group in which two or more groups T3 are condensed with each other, or v) a condensed cyclic group in which at least one group T3 and at least one group T1 are condensed with each other (e.g., the C.sub.3-C.sub.60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, etc.), and
[0422] the ? electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group may be i) a group T4, ii) a condensed cyclic group in which two or more groups T4 are condensed with each other, iii) a condensed cyclic group in which at least one group T4 and at least one group T1 are condensed with each other, iv) a condensed cyclic group in which at least one group T4 and at least one group T3 are condensed with each other, or v) a condensed cyclic group in which at least one group T4, at least one group T1, and at least one group T3 are condensed with each other (e.g., a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.).
[0423] The group T1 may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or a bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group.
[0424] The group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group.
[0425] The group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group.
[0426] The group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
[0427] The term cyclic group, C.sub.3-C.sub.60 carbocyclic group, C.sub.1-C.sub.60 heterocyclic group, ? electron-rich C.sub.3-C.sub.60 cyclic group, or ? electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group as utilized herein refers to a group condensed with any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.), depending on the structure of a formula in connection with which the terms are utilized.
[0428] For example, the benzene group may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the benzene group.
[0429] Non-limiting examples of the monovalent C.sub.3-C.sub.60 carbocyclic group and the monovalent C.sub.1-C.sub.60 heterocyclic group may include a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
[0430] Non-limiting examples of the divalent C.sub.3-C.sub.60 carbocyclic group and the divalent C.sub.1-C.sub.60 heterocyclic group may include a C.sub.3-C.sub.10 cycloalkylene group, a C.sub.1-C.sub.10 heterocycloalkylene group, a C.sub.3-C.sub.10 cycloalkenylene group, a C.sub.1-C.sub.1o heterocycloalkenylene group, a C.sub.6-C.sub.60 arylene group, a C.sub.1-C.sub.60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.
[0431] The term C.sub.1-C.sub.60 alkyl group as utilized herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has 1 to 60 carbon atoms, and non-limiting examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, and/or the like.
[0432] The term C.sub.1-C.sub.60 alkylene group as utilized herein refers to a divalent group having the same structure as the C.sub.1-C.sub.60 alkyl group.
[0433] The term C.sub.2-C.sub.60 alkenyl group as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C.sub.2-C.sub.60 alkyl group, and non-limiting examples thereof may include an ethenyl group, a propenyl group, a butenyl group, and/or the like.
[0434] The term C.sub.2-C.sub.60 alkenylene group as utilized herein refers to a divalent group having the same structure as the C.sub.2-C.sub.60 alkenyl group.
[0435] The term C.sub.2-C.sub.60 alkynyl group as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C.sub.2-C.sub.60 alkyl group, and non-limiting examples thereof may include an ethynyl group, a propynyl group, and/or the like.
[0436] The term C.sub.2-C.sub.60 alkynylene group as utilized herein refers to a divalent group having the same structure as the C.sub.2-C.sub.60 alkynyl group.
[0437] The term C.sub.1-C.sub.60 alkoxy group as utilized herein refers to a monovalent group represented by -OA.sub.101 (wherein A.sub.101 is the C.sub.1-C.sub.60 alkyl group), and non-limiting examples thereof may include a methoxy group, an ethoxy group, an isopropyloxy group, and/or the like.
[0438] The term C.sub.3-C.sub.10 cycloalkyl group as utilized herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and/or the like.
[0439] The term C.sub.3-C.sub.10 cycloalkylene group as utilized herein refers to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkyl group.
[0440] The term C.sub.1-C.sub.10 heterocycloalkyl group as utilized herein refers to a monovalent cyclic group that has 1 to 10 carbon atoms and further includes, in addition to carbon atoms, at least one heteroatom as a ring-forming atom, and non-limiting examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and/or the like.
[0441] The term C.sub.1-C.sub.10 heterocycloalkylene group as utilized herein refers to a divalent group having the same structure as the C.sub.1-C.sub.10 heterocycloalkyl group.
[0442] The term C.sub.3-C.sub.10 cycloalkenyl group as utilized herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and/or the like.
[0443] The term C.sub.3-C.sub.10 cycloalkenylene group as utilized herein refers to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkenyl group.
[0444] The term C.sub.1-C.sub.10 heterocycloalkenyl group as utilized herein refers to a monovalent cyclic group that has 1 to 10 carbon atoms, at least one heteroatom as a ring-forming atom, in addition to carbon atoms, and at least one double bond in the ring thereof. Non-limiting examples of the C.sub.1-C.sub.10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and/or the like.
[0445] The term C.sub.1-C.sub.10 heterocycloalkenylene group as utilized herein refers to a divalent group having the same structure as the C.sub.1-C.sub.10 heterocycloalkenyl group.
[0446] The term C.sub.6-C.sub.60 aryl group as utilized herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms.
[0447] The term C.sub.6-C.sub.60 arylene group as utilized herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms.
[0448] Non-limiting examples of the C.sub.6-C.sub.60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, and/or the like.
[0449] When the C.sub.6-C.sub.60 aryl group and the C.sub.6-C.sub.60 arylene group each include two or more rings, the two or more rings may be condensed with each other.
[0450] The term C.sub.1-C.sub.60 heteroaryl group as utilized herein refers to a monovalent group that has a heterocyclic aromatic system of 1 to 60 carbon atoms and further includes, in addition to carbon atoms, at least one heteroatom as a ring-forming atom.
[0451] The term C.sub.1-C.sub.60 heteroarylene group as utilized herein refers to a divalent group that has a heterocyclic aromatic system of 1 to 60 carbon atoms and further includes, in addition to carbon atoms, at least one heteroatom as a ring-forming atom.
[0452] Non-limiting examples of the C.sub.1-C.sub.60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a naphthyridinyl group, and/or the like.
[0453] When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60 heteroarylene group each include two or more rings, the two or more rings may be condensed with each other.
[0454] The term monovalent non-aromatic condensed polycyclic group as utilized herein refers to a monovalent group that has two or more rings condensed with each other, only carbon atoms (e.g., 8 to 60 carbon atoms) as ring-forming atoms, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indenoanthracenyl group, and/or the like.
[0455] The term polyvalent (e.g., divalent) non-aromatic condensed polycyclic group as utilized herein respectively refers to a polyvalent (e.g., divalent) group having the same structure as the monovalent non-aromatic condensed polycyclic group.
[0456] The term monovalent non-aromatic condensed heteropolycyclic group as utilized herein refers to a monovalent group that has two or more rings condensed with each other, at least one heteroatom other than carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphtho silolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, a benzothienodibenzothiophenyl group, and/or the like.
[0457] The term polyvalent (e.g., divalent) non-aromatic condensed heteropolycyclic group as utilized herein respectively refers to a polyvalent (e.g., divalent group) having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0458] The term C.sub.6-C.sub.60 aryloxy group as utilized herein refers to -OA.sub.102 (wherein A.sub.102 is the C.sub.6-C.sub.60 aryl group).
[0459] The term C.sub.6-C.sub.60 arylthio group as utilized herein refers to -SA.sub.103 (wherein A.sub.103 is the C.sub.6-C.sub.60 aryl group).
[0460] The term C.sub.7-C.sub.60 arylalkyl group as utilized herein refers to -A.sub.104A1.sub.05 (wherein A.sub.104 is a C.sub.1-C.sub.54 alkylene group, and A.sub.105 is a C.sub.6-C.sub.59 aryl group).
[0461] The term C.sub.2-C.sub.60 heteroarylalkyl group as utilized herein refers to -A.sub.106A.sub.107 (wherein A.sub.106 is a C.sub.1-C.sub.59 alkylene group, and A.sub.107 is a C.sub.1-C.sub.59 heteroaryl group).
[0462] The term R.sub.10a as utilized herein refers to:
[0463] deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, or a nitro group;
[0464] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, a C.sub.2-C.sub.60 heteroarylalkyl group, Si(Q.sub.11)(Q.sub.12)(Q.sub.13), N(Q.sub.11)(Q.sub.12), B(Q.sub.11)(Q.sub.12), C(?O)(Q.sub.11), S(?O).sub.2(Q.sub.11), P(?O)(Q.sub.11)(Q.sub.12), or any combination thereof;
[0465] a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, or a C.sub.2-C.sub.60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, a C.sub.2-C.sub.60 heteroarylalkyl group, Si(Q.sub.21)(Q.sub.22)(Q.sub.23), N(Q.sub.21)(Q.sub.22), B(Q.sub.21)(Q.sub.22), C(?O)(Q.sub.21), S(?O).sub.2(Q.sub.21), P(?O)(Q.sub.21)(Q.sub.22), or any combination thereof; or
[0466] Si(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), B(Q.sub.31)(Q.sub.32), C(?O)(Q.sub.31), S(?O).sub.2(Q.sub.31), or P(?O)(Q.sub.31)(Q.sub.32).
[0467] Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23 and Q.sub.31 to Q.sub.33 utilized herein may each independently be: hydrogen; deuterium; F; Cl; Br; I; a hydroxyl group; a cyano group; a nitro group; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxy group; a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C.sub.7-C.sub.60 arylalkyl group; or a C.sub.2-C.sub.60 heteroarylalkyl group.
[0468] The term heteroatom as utilized herein refers to any atom other than a carbon atom. Non-limiting examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0469] The term third-row transition metal as utilized herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.
[0470] The term Ph as utilized herein refers to a phenyl group, the term Me as utilized herein refers to a methyl group, the term Et as utilized herein refers to an ethyl group, the term tert-Bu or Bu.sup.t as utilized herein refers to a tert-butyl group, and the term OMe as utilized herein refers to a methoxy group.
[0471] The term biphenyl group as utilized herein refers to a phenyl group substituted with a phenyl group. In other words, the biphenyl group is a substituted phenyl group having a C.sub.6-C.sub.60 aryl group as a substituent.
[0472] The term terphenyl group as utilized herein refers to a phenyl group substituted with a biphenyl group. In other words, the terphenyl group is a substituted phenyl group having, as a substituent, a C.sub.6-C.sub.60 aryl group substituted with a C.sub.6-C.sub.60 aryl group.
[0473] * and * as utilized herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
[0474] The x-axis, y-axis, and z-axis as utilized herein are not limited to three axes in an orthogonal coordinate system, and may be interpreted in a broad sense including these axes. For example, the x-axis, y-axis, and z-axis may be orthogonal to each other, but the x-axis, y-axis, and z-axis may also refer to different directions that are not orthogonal to each other.
[0475] Hereinafter, compounds according to one or more embodiments and opto-electronic devices according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording B was utilized instead of A utilized in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
Synthesis Example 1-1 (Synthesis of Compound A37)
[0476] ##STR00164##
[0477] 4,4-dimethyl-4H-selenopheno[3,2:5,6]pyrido[3,2,1-jk]carbazole-2-carbaldehyde was suspended in ethanol, 1,3-dimethylpyrimidine-2,4,6-(1H,3H,5H)-trione was added thereto, and the mixture was reacted at 50? C. for 24 hours to obtain a compound. The obtained compound was purified by sublimation to a purity of 99.9%, thereby obtaining Compound A37.
Synthesis Example 1-2 (Synthesis of Compound A44)
[0478] ##STR00165##
[0479] 4,4-dimethyl-4H-selenopheno[3,2:5,6]pyrido[3,2,1-jk]carbazole-2-carbaldehyde was suspended in ethanol, 1-methyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione was added thereto, and the mixture was reacted at 50? C. for 24 hours to obtain a compound. The obtained compound was purified by sublimation to a purity of 99.9% to obtain Compound A44.
Synthesis Example 2-1 (Synthesis of Compound B32)
[0480] Compound B32 (manufactured by Tokyo Chemical Industry) was prepared by sublimation purification.
Synthesis Example 2-2 (Synthesis of Compound B57)
[0481] A mixture of 1,4,5,8,-naphthalenetetracarboxylic dianhydride (1 eq.) and 4-chloroaniline (2.2 eq.) was dissolved in a dimethylformamide (DMF) solvent, and the mixed solution was placed in a two-necked, round-bottomed flask and stirred at 180? C. for 24 hours. Then, after lowering the temperature to room temperature, methanol was added thereto to precipitate the product, which was then filtered to obtain a powdery material. Then, the material was washed several times with methanol and purified by recrystallization utilizing ethyl acetate (EA) and dimethylsulfoxide (DMSO). Then, the obtained product was placed in an oven and dried in a vacuum at 80? C. for 24 hours to obtain Compound B57.
Synthesis Example 3-1 (Synthesis of Compound C1)
[0482] ##STR00166##
##STR00167##
[0483] 2-chloro-9,9-dimethyl-9H-fluorene, 4,4,4,4,5,5,5,5-octamethyl-2,2-bi(1,3,2-dioxaborolane), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)C.sub.12), and potassium acetate was added to 1,4-dioxane, and the mixture was stirred at 110? C. for 8 hours. After completion of the reaction, an extraction process was performed thereon utilizing methylene chloride, and the extracted organic layer was dried utilizing with magnesium sulfate, concentrated, and subjected to column chromatography to obtain Intermediate C1-1. 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine was mixed with Intermediate C1-1 and K.sub.2CO.sub.3, dioxane and water were added thereto, tetrakis(triphenylphosphin)palladium (Pd(PPh.sub.3).sub.4) was added thereto, and the mixture was heated and stirred for 2 hours. After completion of the reaction, the temperature was lowered to room temperature, and the product was filtered. The filtrate was poured into water, an extraction process was performed thereon utilizing EA, and the extracted organic layer was dried utilizing MgSO.sub.4. The dried organic layer was concentrated under reduced pressure and then subjected to column chromatography utilizing EA and hexane as an eluent at a ratio of 1:5 to obtain Compound C1.
Synthesis Example 3-2 (Synthesis of Compound C57)
[0484] ##STR00168##
[0485] Compound C57 was obtained in substantially the same manner as in Synthesis Example 3-1, except that 2-([1,1-biphenyl]-4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine was utilized instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.
Synthesis Example 3-3 (Synthesis of Compound C64)
[0486] ##STR00169##
[0487] Compound C64 was obtained in substantially the same manner as in Synthesis Example 3-1, except that 2-([1,1-biphenyl]-3-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine was utilized instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.
Example 1
[0488] As an anode, a glass substrate with 15 ?/cm.sup.2 (1,200 ?) ITO formed thereon (manufactured by Corning Inc.) was cut to a size of 50 mm?50 mm?0.7 mm, sonicated in isopropyl alcohol and pure water, each for 5 minutes, cleaned by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and then mounted on a vacuum deposition apparatus.
[0489] 2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 100 ?. 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,250 ?.
[0490] Compound A37 was vacuum-deposited on the hole transport layer to form a first layer having a thickness of 100 ?. Compound B32 was vacuum-deposited on the first layer to form a second layer having a thickness of 350 ?. Compound C1 was vacuum-deposited on the second layer to form a buffer layer having a thickness of 50 ?.
[0491] Compound ET1 was vacuum-deposited on the buffer layer to form an electron transport layer having a thickness of 300 ?. LiQ was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 ?. AgMg was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 100 ? thereby completing the manufacture of an opto-electronic device.
##STR00170##
Examples 2 and 3 and Comparative Examples 1 to 4
[0492] Opto-electronic devices were manufactured in substantially the same manner as in Example 1, except that corresponding compounds shown in Table 1 were utilized instead of Compound A37 in forming a first layer included in a photoactive layer, corresponding compounds shown in Table 1 were utilized instead of Compound B32 in forming a second layer included in a photoactive layer, and corresponding compounds shown in Table 1 were utilized instead of Compound C1 in forming a buffer layer. In Table 1, Compound D may be referred to as SubPC, Compound E may be referred to as fullerene 60, and Compound F is a compound in which a triazine group of Compound C1 is changed to a pyrimidine group.
Evaluation Example 1
[0493] To evaluate the characteristics of the opto-electronic devices manufactured in Examples 1 to 3 and Comparative Examples 1 to 4, the external quantum efficiency (EQE) thereof was measured, and the results are shown in Table 1. The external quantum efficiency refers to the ratio of electrical energy generated from energy of irradiated light.
[0494] Light (530 nm) was irradiated to an opto-electronic device by utilizing an external quantum efficiency meter (K3100, McScience, Korea). Current generated during light irradiation was measured utilizing an ammeter (Keithley, Tektronix, USA). The external quantum efficiency (EQE) was calculated utilizing the irradiated light and the measured current.
TABLE-US-00001 TABLE 1 First Second Third compound compound compound EQE (%) Example 1 A37 B32 C1 32.4 Example 2 A44 B57 C57 48.7 Example 3 A44 B32 C64 25.9 Comparative D E F 0.6 Example 1 Comparative A37 B32 F 1.2 Example 2 Comparative A44 E C64 5.3 Example 3 Comparative D B57 C57 3.8 Example 4
##STR00171## ##STR00172## ##STR00173##
[0495] From Table 1, it was confirmed that the opto-electronic device of each of Examples 1 to 3 had excellent or suitable external quantum efficiency compared to the opto-electronic device of each of Comparative Examples 1 to 4.
[0496] According to the one or more embodiments of the present disclosure, an opto-electronic device including all of the first compound, the second compound, and the third compound may have high external quantum efficiency. Accordingly, an electronic apparatus including the opto-electronic device may have improved quality.
[0497] In the present disclosure, singular expressions may include plural expressions unless the context clearly indicates otherwise. It will be further understood that the terms comprise, include, or have when utilized in the present disclosure, specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof. The / utilized below may be interpreted as and or as or depending on the situation.
[0498] Throughout the present disclosure, when a component such as a layer, a film, a region, or a plate is mentioned to be placed on another component, it will be understood that it may be directly on another component or that another component may be interposed therebetween. In some embodiments, directly on may refer to that there are no additional layers, films, regions, plates, etc., between a layer, a film, a region, a plate, etc. and the other part. For example, directly on may refer to two layers or two members are disposed without utilizing an additional member such as an adhesive member therebetween.
[0499] In the present disclosure, although the terms first, second, third, etc., may be utilized herein to describe one or more elements, components, regions, and/or layers, these elements, components, regions, and/or layers should not be limited by these terms. These terms are only utilized to distinguish one component from another component.
[0500] As utilized herein, the singular forms a, an, one, and the are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of may when describing embodiments of the present disclosure refers to one or more embodiments of the present disclosure.
[0501] In the present disclosure, when particles are spherical, diameter indicates a particle diameter or an average particle diameter, and when the particles are non-spherical, the diameter indicates a major axis length or an average major axis length. The diameter (or size) of the particles may be measured utilizing a scanning electron microscope or a particle size analyzer. As the particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer, may be utilized. When the size of the particles is measured utilizing a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of particles whose cumulative volume corresponds to 50 vol % in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.
[0502] As utilized herein, the terms substantially, about, or similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. About 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 of ordinary 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 may mean within one or more standard deviations, or within ?30%, 20%, 10%, 5% of the stated value.
[0503] Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of 1.0 to 10.0 is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
[0504] The opto-electronic device, the light-emitting device, the display apparatus/device, the electronic apparatus, the electronic device, the electronic equipment, or any other relevant devices or components according to embodiments of the present disclosure described herein may be implemented utilizing any suitable hardware, firmware (e.g., an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
[0505] It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims and equivalents thereof.