Organic light-emitting device
09822133 · 2017-11-21
Assignee
Inventors
- Myeong-Suk Kim (Yongin, KR)
- Hye-In Jeong (Yongin, KR)
- Seok-Hwan Hwang (Yongin, KR)
- Sam-Il Kho (Yongin, KR)
- Ja-Hyun Im (Yongin, KR)
Cpc classification
C09B57/008
CHEMISTRY; METALLURGY
H10K85/631
ELECTRICITY
C07D209/70
CHEMISTRY; METALLURGY
H10K85/6574
ELECTRICITY
H10K85/6572
ELECTRICITY
C09B69/008
CHEMISTRY; METALLURGY
H10K85/636
ELECTRICITY
C09B23/02
CHEMISTRY; METALLURGY
International classification
C09B23/02
CHEMISTRY; METALLURGY
C07D209/70
CHEMISTRY; METALLURGY
Abstract
Provided is an organic light-emitting device including a first electrode, a second electrode, an emission layer between the first electrode and the second electrode, and a hole transport region between the first electrode and the emission layer, wherein the hole transport region includes an auxiliary layer, the auxiliary layer including at least one amine-based compound represented by Formula 1: ##STR00001##
where R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16, X.sub.11, L.sub.11, L.sub.12, L.sub.13, a11, a12, a13, b15, and b16 are as defined in the specification.
Claims
1. An organic light-emitting device, comprising: a first electrode; a second electrode; an emission layer between the first electrode and the second electrode; and a hole transport region between the first electrode and the emission layer, wherein the hole transport region includes an auxiliary layer, the auxiliary layer including at least one amine-based compound represented by Formula 1: ##STR00076## in Formula 1, X.sub.11 is selected from an oxygen atom, a sulfur atom, C(R.sub.17)(R.sub.18), and N(R.sub.17); L.sub.11 to L.sub.13 are each independently selected from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkylene group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkenylene group, a substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or an unsubstituted C.sub.2-C.sub.60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group; a11 is selected from 1, 2, and 3; a12 and a13 are each independently selected from 0, 1, 2, and 3; R.sub.11 to R.sub.14 are each independently selected from a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, and —N(Q.sub.1)(Q.sub.2), and —B(Q.sub.6)(Q.sub.7); R.sub.15 and R.sub.16 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, and —N(Q.sub.1)(Q.sub.2), and —B(Q.sub.6)(Q.sub.7); b15 is selected from 1, 2, and 3; b16 is selected from 1, 2, 3, and 4; at least one substituent of the substituted C.sub.3-C.sub.10 cycloalkylene group, the substituted C.sub.3-C.sub.10 heterocycloalkylene group, the substituted C.sub.3-C.sub.10 cycloalkenylene group, the substituted C.sub.3-C.sub.10 heterocycloalkenylene group, the substituted C.sub.5-C.sub.60 arylene group, the substituted C.sub.2-C.sub.60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic hetero-condensed polycyclic group, the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.3-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.3-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.2-C.sub.60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, or the substituted monovalent non-aromatic hetero-condensed polycyclic group is selected from a deuterium atom, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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, and a C.sub.1-C.sub.60 alkoxy 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, and a C.sub.1-C.sub.60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hetero-condensed polycyclic group, —N(Q.sub.11)(Q.sub.12), and —B(Q.sub.16)(Q.sub.17); a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group; a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, —N(Q.sub.21)(Q.sub.22), and —B(Q.sub.26)(Q.sub.27); and —N(Q.sub.31)(Q.sub.32), and —B(Q.sub.36)(Q.sub.37); wherein, R.sub.17, R.sub.18, Q.sub.1, Q.sub.2, Q.sub.6, Q.sub.7, Q.sub.11, Q.sub.16, Q.sub.17, Q.sub.21, Q.sub.22, Q.sub.26, Q.sub.27, Q.sub.31, Q.sub.32, Q.sub.36, and Q.sub.37 are each independently selected from a C.sub.1-C.sub.60 alkyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
2. The organic light-emitting device as claimed in claim 1, wherein X.sub.11 is selected from an oxygen atom, a sulfur atom, and N(R.sub.17).
3. The organic light-emitting device as claimed in claim 1, wherein L.sub.11 to L.sub.13 are each independently selected from groups represented by Formulae 3-1 to 3-30: ##STR00077## ##STR00078## ##STR00079## in Formulae 3-1 to 3-30, symbols * and *′ are binding sites to neighboring atoms; Y.sub.1 is O, S, C(Z.sub.3)(Z.sub.4), N(Z.sub.5), or Si(Z.sub.6)(Z.sub.7); Z.sub.1 to Z.sub.7 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a O—C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, d1 is an integer selected from 1 to 4; d2 is an integer selected from 1 to 3; d3 is an integer selected from 1 to 6; d4 is an integer selected from 1 to 8; d5 is 1 or 2; and d6 is an integer selected from 1 to 5.
4. The organic light-emitting device as claimed in claim 1, wherein L.sub.11 to L.sub.13 are each independently selected from groups represented by Formulae 4-1 to 4-21: ##STR00080## ##STR00081## ##STR00082## in Formulae 4-1 to 4-21, symbols * and *′ are binding sites to neighboring atoms.
5. The organic light-emitting device as claimed in claim 1, wherein a11 is 1 or 2.
6. The organic light-emitting device as claimed in claim 1, wherein a12 and a13 are each independently 0 or 1.
7. The organic light-emitting device as claimed in claim 1, wherein R.sub.11 to R.sub.14 are each independently selected from a C.sub.1-C.sub.20 alkyl group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.5-C.sub.60 aryl group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group; and a C.sub.1-C.sub.20 alkyl group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.1-C.sub.20 alkyl group substituted with —F, —Cl, —Br, —I, a C.sub.6-C.sub.60 aryl group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
8. The organic light-emitting device as claimed in claim 1, wherein R.sub.11 to R.sub.14 are each independently selected from a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group; and a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.20 alkoxy group, a C.sub.1-C.sub.20 alkyl group substituted with —F, —Cl, —Br, —I, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coroneryl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a benzocarbazolyl group; and Q.sub.23 to Q.sub.25 are each independently selected from a C.sub.1-C.sub.20 alkyl group, a phenyl group, a naphthyl group, and a pyridinyl group.
9. The organic light-emitting device as claimed in claim 1, wherein R.sub.11 to R.sub.14 are each independently are selected from a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl, an indolyl, a quinolinyl group, an isoquinolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, a triazolyl group, a tetrazolyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group; and a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl, an indolyl, a quinolinyl group, an isoquinolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, a triazolyl group, a tetrazolyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from a deuterium atom, —F, —Cl, —Br, —I, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, —CF.sub.3, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl, an indolyl, an indazolyl, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.
10. The organic light-emitting device as claimed in claim 1, wherein R.sub.11 to R.sub.14 are each independently selected from groups represented by Formulae 6-1 to 6-5: ##STR00083## in Formulae 6-1 to 6-5, symbol * is a binding site to a neighboring atom.
11. The organic light-emitting device as claimed in claim 1, wherein R.sub.15 and R.sub.16 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, 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.10 cycloalkyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
12. The organic light-emitting device as claimed in claim 1, wherein R.sub.17 and R.sub.18 are each independently selected from a methyl group, an ethyl group, an n-propyl group, a phenyl group, a naphthyl group, and a pyridinyl group.
13. The organic light-emitting device as claimed in claim 1, wherein the amine-based compound is represented by Formula 1A: ##STR00084## in Formula 1A, X.sub.11, L.sub.11 to L.sub.13, a11 to a13, and R.sub.11 to R.sub.14 have the same meaning as in Formula 1.
14. The organic light-emitting device as claimed in claim 1, wherein the amine-based compound is selected from Compounds 1A to 9A: ##STR00085## ##STR00086## ##STR00087##
15. The organic light-emitting device as claimed in claim 1, wherein the emission layer and the auxiliary layer are adjacent each other.
16. The organic light-emitting device as claimed in claim 1, wherein the hole transport region includes a carbazole-based compound represented by Formula 201A: ##STR00088## in Formula 201A, L.sub.201 to L.sub.203 are each independently selected from a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; xa1 to xa3 are each independently 0 or 1; R.sub.203 and R.sub.211 are each independently selected from a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; R.sub.213 and R.sub.214 are each independently selected from a C.sub.1-C.sub.20 alkyl group and a C.sub.1-C.sub.20 alkoxy group; a C.sub.1-C.sub.20 alkyl group and a C.sub.1-C.sub.20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; R.sub.215 and R.sub.216 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, and a C1-C.sub.20 alkoxy group; a C.sub.1-C.sub.20 alkyl group and a C.sub.1-C.sub.20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and a triazinyl group; and a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group.
17. The organic light-emitting device as claimed in claim 1, wherein the hole transport region further includes a p-dopant.
18. The organic light-emitting device as claimed in claim 16, wherein the hole transport region includes a hole transport layer, the hole transport layer including the carbazole-based compound.
19. The organic light-emitting device as claimed in claim 18, wherein the hole transport layer is adjacent the auxiliary layer.
20. The organic light-emitting device as claimed in claim 1, wherein the organic light-emitting device further includes an electron transport region between the emission layer and the second electrode.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
(1) Features will become apparent to those of skill in the art by describing in detail exemplary embodiments with reference to the attached drawings in which:
(2)
(3)
DETAILED DESCRIPTION
(4) Example embodiments will now be described more fully hereinafter with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.
(5) In the drawing figures, the dimensions of layers and regions may be exaggerated for clarity of illustration. It will also be understood that when a layer or element is referred to as being “on” another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. Further, it will be understood that when a layer is referred to as being “under” another layer, it can be directly under, and one or more intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being “between” two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present.
(6) Expressions such as “at least one of” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
(7) An expression used in the singular encompasses the expression of the plural, unless it has a clearly different meaning in the context.
(8) The amine-based compound may be represented by Formula 1 below:
(9) ##STR00003##
(10) In Formula 1, X.sub.11 may be selected from an oxygen atom, a sulfur atom, C(R.sub.17)(R.sub.18), and N(R.sub.17). R.sub.17 and R.sub.18 are the same as described below.
(11) For example, in Formula 1, X.sub.11 may be selected from an oxygen atom, a sulfur atom, and N(R.sub.17).
(12) In Formula 1, L.sub.11 to L.sub.13 may be each independently selected from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkylene group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkenylene group, a substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group;
(13) at least one substituent of the substituted C.sub.3-C.sub.10 cycloalkylene group, the substituted C.sub.3-C.sub.10 heterocycloalkylene group, the substituted C.sub.3-C.sub.10 cycloalkenylene group, the substituted C.sub.3-C.sub.10 heterocycloalkenylene group, the substituted C.sub.6-C.sub.60 arylene group, the substituted C.sub.2-C.sub.60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, or the substituted divalent non-aromatic hetero-condensed polycyclic group may be selected from
(14) a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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, and a C1-C.sub.60 alkoxy group;
(15) 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, and a C1-C.sub.60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, —N(Q.sub.11)(Q.sub.12), —Si(Q.sub.13)(Q.sub.14)(Q.sub.15), and —B(Q.sub.16)(Q.sub.17);
(16) a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group;
(17) a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, —N(Q.sub.21)(Q.sub.22), —Si(Q.sub.23)(Q.sub.24)(Q.sub.25), and —B(Q.sub.26)(Q.sub.27); and
(18) —N(Q.sub.31)(Q.sub.32), —Si(Q.sub.33)(Q.sub.34)(Q.sub.35), and —B(Q.sub.36)(Q.sub.37); wherein,
(19) Q.sub.11 to Q.sub.17, Q.sub.21 to Q.sub.27 and Q.sub.31 to Q.sub.37 may be each independently selected from a C.sub.1-C.sub.60 alkyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
(20) For example, in Formula 1, L.sub.11 to L.sub.13 may be each independently selected from a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isooxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzooxazolylene group, an isobenzooxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazolylene group, and an imidazopyridinylene group; and
(21) a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isooxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzooxazolylene group, an isobenzooxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazolylene group, and an imidazopyridinylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group.
(22) In an implementation, in Formula 1, L.sub.11 to L.sub.13 may be each independently groups selected from Formulae 3-1 to 3-30 below:
(23) ##STR00004## ##STR00005## ##STR00006##
(24) in Formulae 3-1 to 3-30,
(25) Y.sub.1 may be O, S, a C(Z.sub.3)(Z.sub.4), N(Z.sub.5), or Si(Z.sub.6)(Z.sub.7);
(26) Z.sub.1 to Z.sub.7 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group,
(27) d1 may be an integer selected from 1 to 4;
(28) d2 may be an integer selected from 1 to 3;
(29) d3 may be an integer selected from 1 to 6;
(30) d4 may be an integer selected from 1 to 8;
(31) d5 may be 1 or 2;
(32) d6 may be an integer selected from 1 to 5.
(33) In another embodiment, in Formula 1, L.sub.11 to L.sub.13 may be each independently groups selected from Formulae 4-1 to 4-21:
(34) ##STR00007## ##STR00008## ##STR00009##
(35) In Formulae 4-1 to 4-21
(36) * and *′ are binding sites to neighboring atoms.
(37) In Formula 1, a11 represents a number of L.sub.11s and may be selected from 1, 2 and 3. For example, in Formula 1, a11 may be selected from 1 and 2, for example. When a11 is 2 or greater, a plurality of L.sub.11s may be the same or different.
(38) In Formula 1, a12 represents a number of L.sub.12s and may be selected from 0, 1, 2, and 3. In Formula 1, when a12 is 0, -(L.sub.12).sub.a12- may be a single bond. For example, in Formula 1, a12 may be selected from 0 and 1, for example. When a12 is 2 or greater, a plurality of L.sub.12s may be the same or different.
(39) In Formula 1, a13 represents a number of L.sub.13s and may be selected from 0, 1, 2, and 3. In Formula 1, when a13 is 0, -(L.sub.13).sub.a13- may be a single bond. For example, in Formula 1, a13 may be selected from 0 and 1, for example. When a13 is 2 or greater, a plurality of L.sub.13s may be the same or different.
(40) In Formula 1, R.sub.11 to R.sub.14 may be each independently selected from a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, and —N(Q.sub.1)(Q.sub.2), —Si(Q.sub.3)(Q.sub.4)(Q.sub.5), and —B(Q.sub.6)(Q.sub.7);
(41) at least one substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.3-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.3-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.2-C.sub.60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic hetero-condensed polycyclic group may be selected from
(42) a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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, and a C.sub.1-C.sub.60 alkoxy group;
(43) 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, and a C.sub.1-C.sub.60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, —N(Q.sub.11)(Q.sub.12), —Si(Q.sub.13)(Q.sub.14)(Q.sub.15), and —B(Q.sub.16)(Q.sub.17);
(44) a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group;
(45) a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, —N(Q.sub.21)(Q.sub.22), —Si(Q.sub.23)(Q.sub.24)(Q.sub.25) and —B(Q.sub.26)(Q.sub.27); and
(46) —N(Q.sub.31)(Q.sub.32), —Si(Q.sub.33)(Q.sub.34)(Q.sub.35) and —B(Q.sub.36)(Q.sub.37); wherein,
(47) Q.sub.1 to Q.sub.7, Q.sub.11 to Q.sub.17, Q.sub.21 to Q.sub.27, and Q.sub.31 to Q.sub.37 may be each independently selected from a C.sub.1-C.sub.60 alkyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
(48) For example, in Formula 1, R.sub.11 to R.sub.14 may be each independently selected from a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzooxazolyl group, a triazolyl group, a tetrazolyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group; and
(49) a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzooxazolyl group, a triazolyl group, a tetrazolyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from a deuterium atom, —F, —Cl, —Br, —I, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, —Si(CH.sub.3).sub.3, —Si(Ph).sub.3, —CF.sub.3, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl, an indolyl, an indazolyl, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, for example.
(50) In an implementation, in Formula 1, R.sub.11 to R.sub.14 may be each independently groups selected from Formulae 6-1 to 6-5 below:
(51) ##STR00010##
(52) in Formulae 6-1 to 6-5,
(53) * is a binding site to a neighboring atom.
(54) In Formula 1, R.sub.15 and R.sub.16 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.3-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, and —N(Q.sub.1)(Q.sub.2), —Si(Q.sub.3)(Q.sub.4)(Q.sub.5), and —B(Q.sub.6)(Q.sub.7);
(55) at least one substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.3-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.3-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.2-C.sub.60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic hetero-condensed polycyclic group, may be each independently selected from
(56) a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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, and a C.sub.1-C.sub.60 alkoxy group;
(57) 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, and a C.sub.1-C.sub.60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, —N(Q.sub.11)(Q.sub.12), —Si(Q.sub.13)(Q.sub.14)(Q.sub.15), and —B(Q.sub.16)(Q.sub.17);
(58) a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group;
(59) a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, —N(Q.sub.21)(Q.sub.22), —Si(Q.sub.23)(Q.sub.24)(Q.sub.25) and —B(Q.sub.26)(Q.sub.27); and
(60) —N(Q.sub.31)(Q.sub.32), —Si(Q.sub.33)(Q.sub.34)(Q.sub.35) and —B(Q.sub.36)(Q.sub.37); wherein,
(61) Q.sub.1 to Q.sub.7, Q.sub.11 to Q.sub.17, Q.sub.21 to Q.sub.27 and Q.sub.31 to Q.sub.37 may be each independently selected from a C.sub.1-C.sub.60 alkyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
(62) For example, in Formula 1, R.sub.15 and R.sub.16 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, 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.10 cycloalkyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
(63) In another implementation, in Formula 1, R.sub.15 and R.sub.16 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br—, —I, a cyano group, a nitrile group, a methyl group, a methoxy group, a phenyl group, a naphthyl group, and a phenoxy group.
(64) In Formula 1, b15 represents a number of R.sub.15s and may be an integer selected from 1, 2, and 3. When b15 is an integer that is 2 or greater, a plurality of R.sub.15s may be the same or different.
(65) In Formula 1, b16 represents a number of R.sub.16s and may be an integer selected from 1, 2, 3, and 4. When b16 is an integer that is 2 or greater, a plurality of R.sub.16s may be the same or different.
(66) In Formula 1, R.sub.17 and R.sub.18 may be each independently selected from a C.sub.1-C.sub.60 alkyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.2-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
(67) For example, in Formula 1, R.sub.17 and R.sub.18 may be each independently selected from a methyl group, an ethyl group, an n-propyl group, a phenyl group, a naphthyl group, and a pyridinyl.
(68) According to an embodiment, the amine-based compound may be represented by Formula 1A below:
(69) ##STR00011##
(70) In Formula 1A, X.sub.11, L.sub.11 to L.sub.13, a11 to a13, and R.sub.11 to R.sub.14 may be the same as described above.
(71) In an implementation, when the amine-based compound is represented by Formula 1A above, in Formula 1A, L.sub.11 to L.sub.13 may be each independently groups selected from Formulae 4-1 to 4-21 above.
(72) In an implementation, when the amine-based compound is represented by Formula 1A above, in Formula 1A, R.sub.11 to R.sub.14 may be each independently groups selected from Formulae 6-1 to 6-5 above.
(73) In another implementation, the amine-based compound may be selected from Compounds 1A to 9A:
(74) ##STR00012## ##STR00013## ##STR00014##
(75) An organic light-emitting device including the amine-based compound represented by Formula 1 above may have improved efficiency and improved lifespan.
(76) The amine-based compound represented by Formula 1 above may be synthesized by an organic synthesis method known in the art. The synthesis method of the amine-based compound may be understood by one of ordinary skill in the art based on the examples described below.
(77) The amine-based compound represented by Formula 1 above may be used between a pair of electrodes in an organic light-emitting device. For example, the amine-based compound may be used in the hole transport region, for example, in an auxiliary layer.
(78) Accordingly, provided is an organic light-emitting device including a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one amine-based compound represented by Formula 1 described above.
(79) As used herein, the expression “(organic layer) includes at least one amine-based compound” may be construed as “(organic layer) may include one amine-based compound as defined by Formula 1 or two or more different amine-based compounds as defined by Formula 1”.
(80) For example, the organic layer may only include Compound 1A as the amine-based compound. In this regard, Compound 1A may be present in a hole transport region of the organic light-emitting device. In another implementation, the organic layer may include both Compound 1A and Compound 2A as the amine-based compound. In this regard, Compound 1A and Compound 2A be present in the same layer (for example, in the hole transport region) or in different layers (for example, in the hole transport region and the emission layer (EML), respectively).
(81) The organic layer may include i) the hole transport region disposed between the first electrode and the EML and including at least one of a hole injection layer (HIL), a hole transport layer (HTL), an auxiliary layer (AL), and an electron-blocking layer (EBL); and ii) an electron transport region disposed between the EML and the second electrode and including at least one of the EBL, the ETL, and the EIL.
(82) As used herein, the expression, the “organic layer” may refer to a single layer and/or a multi-layer disposed between the first electrode and the second electrode in the organic light-emitting device.
(83)
(84) The organic light-emitting device 10 may include a first electrode 110, an organic layer 150, and a second electrode 190.
(85) A substrate may be additionally disposed under the first electrode 110 and on the second electrode 190. The substrate may be a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
(86) The first electrode 110 may be formed by, for example, depositing or sputtering a first electrode material on the substrate. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials with a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for the first electrode 110 may be a transparent material with high conductivity. Examples of such a material include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), and zinc oxide (ZnO). As the first electrode material, magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like may be used to form the first electrode 110, which is a semi-transmissive electrode or a reflective electrode.
(87) The first electrode 110 may have a single-layer structure or a multi-layer structure. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
(88) The organic layer 150 may be disposed on the first electrode 110. The organic layer 150 may include the EML 160.
(89) The organic layer 150 may further include a hole transport region 130 disposed between the first electrode and the EML and an electron transport region 180 disposed between the EML and the second electrode.
(90) The hole transport region may include at least one from the HIL, the HTL, the AL, and the EBL. The electron transport region may include at least one from the HBL, the ETL, and the EIL.
(91) The hole transport region may have a single-layered structure formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure formed of a plurality of different materials.
(92) For example, the hole transport region may have a single-layered structure formed of a plurality of different materials or a structure in which HIL/HTL, HIL/HTL/AL, HIL/AL, HTL/AL or HIL/HTL/EBL are sequentially layered on the first electrode 110.
(93) When the hole transport region includes the HIL, the HIL may be formed on the first electrode 110 by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, laser induced thermal imaging (LITI), or the like.
(94) When the HIL is formed using vacuum deposition, vacuum deposition conditions may vary according to the compound that is used to form the HIL and the desired structure of the HIL to be formed. For example, vacuum deposition may be performed at a temperature of about 100° C. to about 500° C., a pressure of about 10.sup.−8 torr to about 10.sup.−3 torr, and a deposition rate of about 0.01 to about 100 Å/sec. When the HIL is formed using spin coating, the coating conditions may vary according to the compound that is used to form the HIL and the desired structure of the HIL to be formed. For example, the coating rate may be in the range of about 2000 rpm to about 5000 rpm, and a temperature of a heat treatment in the range of about 80° C. to about 200° C. When the hole transport region includes the HTL, the HTL may be formed on the first electrode 110 by using various methods such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, LITI, or the like. The deposition and coating conditions may be similar to those used for the formation of the HIL.
(95) The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-NPB, TAPC, 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), or (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below and a compound represented by Formula 202 below:
(96) ##STR00015## ##STR00016## ##STR00017##
(97) in Formulae 201 and 202,
(98) descriptions of L.sub.201 to L.sub.205 may be each independently understood by referring to the description for L.sub.11 in Formula 1;
(99) xa1 to xa4 may be each independently selected from 0, 1, 2, and 3;
(100) xa5 may be selected from 1, 2, 3, 4, and 5; and
(101) descriptions of R.sub.201 to R.sub.205 may be each independently understood by referring to the description of R.sub.11 in Formula 1.
(102) For example, in Formulae 201 and 202,
(103) L.sub.201 to L.sub.205 may be each independently selected from a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, benzofluorene, dibenzofluorene, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and
(104) a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
(105) xa1 to xa4 may be each independently selected from 0, 1, or 2;
(106) xa5 may be selected from 1, 2, or 3;
(107) R.sub.201 to R.sub.205 may be each independently selected from a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
(108) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, an azulenyl, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, for example.
(109) The compound represented by Formula 201 above may be represented by Formula 201A below:
(110) ##STR00018##
(111) For example, the compound represented by Formula 201 above may be represented by Formula 201A-1 below:
(112) ##STR00019##
(113) The compound represented by Formula 202 above may be represented by represented by Formula 202A below:
(114) ##STR00020##
(115) in Formulae 201A, 201A-1, and 202A, descriptions of L.sub.201 to L.sub.203, xa1 to xa3, xa5, and R.sub.202 to R.sub.204 may be similar to the description disclosed herein, a description of R.sub.211 may be similar to the description of R.sub.203, and R.sub.213 to R.sub.216 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, and a non-aromatic condensed polycyclic group.
(116) For example, in Formulae 201A, 201A-1, and 202A,
(117) L.sub.201 to L.sub.203 may be each independently selected from a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and
(118) a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
(119) xa1 to xa3 may be each independently 0 or 1;
(120) R.sub.203, R.sub.211 and R.sub.212 may be each independently selected from a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
(121) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
(122) R.sub.213 and R.sub.214 may be each independently selected from a C.sub.1-C.sub.20 alkyl group and a C1-C.sub.20 alkoxy group;
(123) a C.sub.1-C.sub.20 alkyl group and a C1-C.sub.20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
(124) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
(125) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
(126) R.sub.215 and R.sub.216 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof,
(127) a C.sub.1-C.sub.20 alkyl group and a C1-C.sub.20 alkoxy group;
(128) a C.sub.1-C.sub.20 alkyl group and a C1-C.sub.20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
(129) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and a triazinyl group; and
(130) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
(131) xa5 may be 1 or 2.
(132) In Formulae 201A and 201A-1, R.sub.213 and R.sub.214 may bind to each other to form a saturated or an unsaturated ring.
(133) The compound represented by Formula 201 below and the compound represented by Formula 202 below may include Compounds HT1 to HT20.
(134) ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027##
(135) A thickness of the hole transport region may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a11 of the HIL and the HTL, a thickness of the HIL may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the HTL may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the HIL and the HTL are within the ranges described above, satisfactory hole transport properties may be obtained without a substantial increase in driving voltage.
(136) The hole transport region may further include a charge-generating material for improving conductivity, in addition to the materials described above. The charge-generating material may be homogeneously or inhomogeneously dispersed in the hole transport region.
(137) The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a compound with a cyano group. Examples of the p-dopant include quinone derivatives, such as tetracyanoquinodimethane (TCNQ), and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxides and molybdenum oxides; and Compound HT-D1 below.
(138) ##STR00028##
(139) The hole transport region may further include an AL, in addition to the HIL and the HTL described above. The AL may be disposed in various locations between the first electrode and the EML. For example, as shown in
(140) HOMO energy of the AL may be disposed between the EML and the HTL to facilitate hole transport. The AL may include an amine-based compound represented by Formula 1A above. In other implementations, the AL may include a material that may be included in the hole transport region, in addition to the amine-based compound represented by Formula 1A above. A thickness of the AL may be about 10 Å to about 100 Å, for example, about 30 Å to about 70 Å.
(141) The hole transport region may further include an EBL. The EBL is a layer that prevents electron injection from the electron transport region.
(142) The EML may be formed on the first electrode 110 or the hole transport region using vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, LITI, or the like. When the EML is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for the formation of the HIL.
(143) When the organic light-emitting device 10 is a full color organic light-emitting device, the organic light-emitting device 10 may be patterned into a red EML, a green EML, and a blue EML according to the EMLs and individual subpixels. In other implementations, the EML may have a structure in which the red EML, the green EML, and the blue EML are layered or a structure in which a red light emission material, green light emission material and blue light emission material are mixed without layer separation.
(144) The EML may include a host and a dopant.
(145) The host may include at least one from TPBi, TBADN, AND (also referred to as “DNA”), CBP, CDBP, and TCP:
(146) ##STR00029## ##STR00030##
(147) In other implementations, the host may include a compound represented by Formula 301 below.
Ar.sub.301-[(L.sub.301).sub.xb1-R.sub.301].sub.xb2 <Formula 301>
(148) In Formula 301,
(149) Ar.sub.301 may be selected from a naphthalene group, a heptalene group, a fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group;
(150) a naphthalene group, a heptalene group, a fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a non-aromatic condensed polycyclic group, and —Si(Q.sub.301)(Q.sub.302)(Q.sub.303) (wherein, Q.sub.301 to Q.sub.303 may be each independently selected from a hydrogen, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.6-C.sub.60 aryl group, and a C.sub.2-C.sub.60 heteroaryl group);
(151) description of L.sub.301 may be similar to the description of L.sub.201;
(152) R.sub.301 may be selected from a C.sub.1-C.sub.20 alkyl group, and a C1-C.sub.20 alkoxy group;
(153) a C.sub.1-C.sub.20 alkyl group, and a C1-C.sub.20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
(154) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazinyl group; and
(155) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
(156) xb1 may be selected from 0, 1, 2, and 3; and
(157) xb2 may be selected from 1, 2, 3, and 4.
(158) For example, in Formula 301,
(159) L.sub.301 may be selected from a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, and a chrysenylene group; and
(160) a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, and a chrysenylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group;
(161) R.sub.301 may be selected from a C.sub.1-C.sub.20 alkyl group and a C.sub.1-C.sub.20 alkoxy group;
(162) a C.sub.1-C.sub.20 alkyl group, and a C.sub.1-C.sub.20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group;
(163) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group; and
(164) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group, for example.
(165) For example, the host may include a compound represented by Formula 301A below:
(166) ##STR00031##
(167) In Formula 301A, descriptions of substituents may be similar to the descriptions above.
(168) The compound represented by Formula 301 may include at least one from Compounds H1 to H42:
(169) ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040##
(170) In other implementations, the host may include at least one from Compounds H43 to H49:
(171) ##STR00041## ##STR00042##
(172) The dopant may include the amine-based compound represented by Formula 1A above. The dopant may include at least one of a fluorescent dopant and a phosphorescent dopant, in addition to the amine-based compound represented by Formula 1A above.
(173) The phosphorescent dopant may include an organic metal complex represented by Formula 401 below:
(174) ##STR00043##
(175) In Formula 401,
(176) M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm);
(177) X.sub.401 to X.sub.404 may be each independently nitrogen or carbon;
(178) A.sub.401 ring and A.sub.402 ring may be each independently selected from a substituted or unsubstituted benzene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted spiro-fluorene group, a substituted or unsubstituted indene group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted thiopene group, a substituted or unsubstituted furan group, a substituted or unsubstituted imidazole group, a substituted or unsubstituted pyrazole group, a substituted or unsubstituted thiazole group, a substituted or unsubstituted isothiazole group, a substituted or unsubstituted oxazole group, a substituted or unsubstituted isooxazole group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted benzoquinoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzoimidazole group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiopene group, a substituted or unsubstituted isobenzothiopene group, a substituted or unsubstituted benzooxazole group, a substituted or unsubstituted isobenzooxazole group, a substituted or unsubstituted triazole group, a substituted or unsubstituted oxadiazole group, a substituted or unsubstituted triazine group, a substituted or unsubstituted dibenzofuran group, and a substituted or unsubstituted dibenzothiopene group;
(179) at least one substituent of the substituted benzene group, the substituted naphthalene group, the substituted fluorene group, the substituted spiro-fluorene group, the substituted indene group, the substituted pyrrole group, the substituted thiopene group, the substituted furan group, the substituted imidazole group, the substituted pyrazole group, the substituted thiazole group, the substituted isothiazole group, the substituted oxazole group, the substituted isooxazole group, the substituted pyridine group, the substituted pyrazine group, the substituted pyrimidine group, the substituted pyridazine group, the substituted quinoline group, the substituted isoquinoline group, the substituted benzoquinoline group, the substituted quinoxaline group, the substituted quinazoline group, the substituted carbazole group, the substituted benzoimidazole group, the substituted benzofuran group, the substituted benzothiopene group, the substituted isobenzothiopene group, the substituted benzooxazole group, the substituted isobenzooxazole group, the substituted triazole group, the substituted oxadiazole group, the substituted triazine group, the substituted dibenzofuran group, and the substituted dibenzothiopene group may be selected from
(180) a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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, and a C1-C.sub.60 alkoxy group;
(181) 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, and a C1-C.sub.60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a non-aromatic condensed polycyclic group, —N(Q.sub.401)(Q.sub.402), —Si(Q.sub.403)(Q.sub.404)(Q.sub.405) and —B(Q.sub.406)(Q.sub.407);
(182) a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, and a non-aromatic condensed polycyclic group;
(183) a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a non-aromatic condensed polycyclic group, —N(Q.sub.411)(Q.sub.412), —Si(Q.sub.413)(Q.sub.414)(Q.sub.415), and —B(Q.sub.416)(Q.sub.417); and
(184) —N(Q.sub.421)(Q.sub.422), —Si(Q.sub.423)(Q.sub.424)(Q.sub.425), and —B(Q.sub.426)(Q.sub.427);
(185) L.sub.401 may be an organic ligand;
(186) xc1 may be 1, 2, or 3; and
(187) xc2 may be 0, 1, 2, or 3.
(188) L.sub.401 may be any one of a monovalent, a divalent, or a trivalent organic ligand.
(189) For example, L.sub.401 may be selected from a halogen ligand (such as Cl and F), a diketone ligand (such as acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2,6,6-tetramethyl-3,5-heptanedionate, and hexafluoroacetonate), a carboxylic acid ligand (such as picolinate, dimethyl-3-pyrazolecarboxylate, and benzoate), a carbon monoxide ligand, an isonitrile group ligand, a cyano group ligand, and a phosphorus ligand (such as phosphine and phosphaite).
(190) In Formula 401, when A.sub.401 has two or more substituents, the two or more substituents of A.sub.401 may bind to each other to form a saturated ring or an unsaturated ring.
(191) In Formula 401, when A.sub.402 has two or more substituents, the two or more substituents of A.sub.402 may bind to each other to form a saturated ring or an unsaturated ring.
(192) In Formula 401, when xc1 is two or greater, a plurality of ligands of Formula 401
(193) ##STR00044##
may be the same or different. In Formula 401, when xc1 is two or greater, A.sub.401 and A.sub.402 may be connected to neighboring A.sub.401 and A.sub.402 either directly or via a linker (such as a C.sub.1-C.sub.5 alkylene group and —N(R′)— (wherein, R′ may be a C.sub.1-C.sub.10 alkyl group or a C.sub.6-C.sub.20 aryl group), or —C(═O)—).
(194) For example, the phosphorescent dopant may include at least one selected from Compounds PD1 to PD74:
(195) ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059##
(196) In other implementations, the phosphorescent dopant may include PtOEP below:
(197) ##STR00060##
(198) The fluorescent dopant may include at least one selected from DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T below.
(199) ##STR00061##
(200) In other implementations, the fluorescent dopant may include a compound represented by Formula 501 below:
(201) ##STR00062##
(202) In Formula 501,
(203) Ar.sub.501 may be selected from a naphthalene group, a heptalene group, a fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group;
(204) a naphthalene group, a heptalene group, a fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a non-aromatic condensed polycyclic group, and —Si(Q.sub.501)(Q.sub.502)(Q.sub.503) (wherein, Q.sub.501 to Q.sub.503 may be each independently selected from a hydrogen, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.6-C.sub.60 aryl group, and a C.sub.2-C.sub.60 heteroaryl group);
(205) L.sub.501 to L.sub.503 may have the same meaning as L.sub.201 in Formula 201 above;
(206) R.sub.501 and R.sub.502 may be each independently selected from a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
(207) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl and a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
(208) xd1 to xd3 may be each independently selected from 0, 1, 2, and 3; and
(209) xb4 may be selected from 1, 2, 3, and 4.
(210) The fluorescent dopant may include at least one from Compounds FD1 to FD8:
(211) ##STR00063## ##STR00064## ##STR00065##
(212) In the EML, an amount of the dopant may generally be selected from a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, as an example.
(213) A thickness of the EML may be about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the EML satisfies the range described above, the EML may show excellent emission properties without a substantial increase in driving voltage.
(214) The electron transport region may be disposed on the EML.
(215) The electron transport region may include an EBL, an ETL, and an EIL, for example.
(216) For example, the electron transport region may have a structure in which the ETL/EIL or the HBL/ETL/EIL are sequentially layered from the EML.
(217) The electron transport region may include an HBL. When the EML includes a phosphorescent dopant, the HBL may be formed to prevent diffusion of triplet excitons or holes into the ETL.
(218) When the electron transport region includes the HBL, the HBL may be formed on the EML by using vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and LITI. When the HBL is formed by using vacuum deposition and spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL.
(219) The HBL may, for example, include at least one selected from BCP and Bphen.
(220) ##STR00066##
(221) A thickness of the HBL may be from about 20 Å to about 1,000 Å, and in some implementations, may be from about 30 Å to about 300 Å. When the thickness of the HBL is within these ranges, the HBL may have an improved hole blocking ability without a substantial increase in driving voltage.
(222) The electron transport region may include an ETL. The ETL may be formed on the EML or the HBL using methods such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and LITI. When the ETL is formed using vacuum deposition and spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL.
(223) The ETL may further include at least one from BCP, Bphen, depicted above, and Alq.sub.3, Balq, TAZ, and NTAZ below.
(224) ##STR00067##
(225) In other implementations, the ETL may include at least one compound represented by Formula 601 below:
Ar.sub.601-[(L.sub.601).sub.xe1-E.sub.601].sub.xe2 <Formula 601>
(226) In Formula 601,
(227) Ar.sub.601 may be selected from a naphthalene group, a heptalene group, fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and indenoanthracene group;
(228) a naphthalene group, a heptalene group, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, 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.10 cycloalkyl group, a C.sub.3-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.3-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.2-C.sub.60 heteroaryl group, a non-aromatic condensed polycyclic group, and —Si(Q.sub.301)(Q.sub.302)(Q.sub.303) (wherein, Q.sub.301 to Q.sub.303 may be each independently selected from a hydrogen, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.6-C.sub.60 aryl group, and a C.sub.2-C.sub.60 heteroaryl group);
(229) L.sub.601 may have the same meaning as L.sub.201 in Formula 201;
(230) E.sub.601 may be selected from a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group; and
(231) a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group;
(232) xe1 may be selected from 0, 1, 2, and 3; and
(233) xe2 may be selected from 1, 2, 3, and 4.
(234) In other implementations, the ETL may include at least one compound represented by Formula 602 below:
(235) ##STR00068##
(236) In Formula 602,
(237) X.sub.611 may be N or C-(L.sub.611).sub.xe611-R.sub.611, X.sub.612 may be N or C-(L.sub.612).sub.xe612-R.sub.612, X.sub.613 may be N or C-(L.sub.613).sub.xe613-R.sub.613, and at least one of X.sub.611 to X.sub.613 is N;
(238) L.sub.611 to L.sub.616 may have the same meaning as L.sub.201 in Formula 201;
(239) R.sub.611 to R.sub.616 may be each independently selected from a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
(240) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid and a salt thereof, a sulfonic acid and a salt thereof, a phosphoric acid and a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, an azulenyl, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
(241) xe611 to xe616 may be each independently selected from 0, 1, 2, and 3.
(242) The compound represented by Formula 601 and the compound represented by Formula 602 may include at least one of Compounds ET1 to ET15.
(243) ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073##
(244) A thickness of the ETL may be about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the ETL is within the range described above, the ETL may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
(245) The ETL may further include a metal-containing material in addition to the material described above.
(246) The metal-containing material may include a Li complex. The Li complex may, for example, include compound ET-D1 (lithium quinolate: LiQ) or ET-D2 illustrated below.
(247) ##STR00074##
(248) The electron transport region may include an EIL that facilitates electron injection from the second electrode 190.
(249) The EIL may be formed on the ETL by using various methods such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and LITI. When the EIL is formed by vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for forming the HIL. When the EML is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for the formation of the HIL.
(250) The EIL may include at least one selected from LiF, NaCl, CsF, Li.sub.2O, BaO, and LiQ.
(251) A thickness of the EIL may be about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the EIL is within the range described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
(252) The second electrode 190 may be disposed on the organic layer 150 described above. The second electrode 190 may be a cathode, which is an electron injection electrode A material for the second electrode 190 may be a metal, an alloy, an electro conductive compound, or a mixture thereof having a low work function. Examples of the material for the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag). In other implementations, ITO, IZO, or the like may be used as the material for the second electrode 190. The second electrode 190 may be a reflective electrode, semi-transmission electrode, or a transmission electrode.
(253) Hereinabove, the organic light-emitting device was described with reference to
(254) As used herein, the term “C.sub.1-C.sub.60 alkyl group” refers to a linear or aliphatic C.sub.1-C.sub.60 hydrocarbon monovalent group, Examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. As used herein, the term “C.sub.1-C.sub.60 alkylene group” refers to a divalent group having the same structure as the C.sub.1-C.sub.60 alkyl group.
(255) As used herein, the term “C.sub.1-C.sub.60 alkoxy group” refers to a monovalent group having a formula of —OA.sub.101 (wherein, A.sub.101 is the C.sub.1-C.sub.60 alkyl group). Examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
(256) As used herein, the term “C.sub.2-C.sub.60 alkenyl group (or C.sub.2-C.sub.60 alkenyl group)” refers to a C.sub.2-C.sub.60 alkyl group having one or more carbon-carbon double bonds at a center or end thereof. Examples of the unsubstituted C.sub.2-C.sub.60 alkenyl group include an ethenyl group, a propenyl group, and a butenyl group. As used herein, the term “C.sub.2-C.sub.60 alkenylene group” refers to a divalent group having the same structure as the C.sub.2-C.sub.60 alkenyl group.
(257) As used herein, the term “C.sub.2-C.sub.60 alkynyl group” refers to an unsubstituted C.sub.2-C.sub.60 alkyl group having one or more carbon-carbon triple bonds at a center or end thereof. Examples of the C.sub.2-C.sub.60 alkynyl group include an ethynyl group, a propynyl group, and the like. As used herein, the term “C.sub.2-C.sub.60 alkynylene group” refers to a divalent group having the same structure as the C.sub.2-C.sub.60 alkynyl group.
(258) As used herein, the term “C.sub.3-C.sub.10 cycloalkyl group” refers to a C.sub.3-C.sub.10 monovalent hydrocarbon monocyclic group. Examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. As used herein, the term “C.sub.3-C.sub.10 cycloalkylene group” refers to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkyl group.
(259) As used herein, the term “C.sub.3-C.sub.10 heterocycloalkyl group” refers to a C.sub.3-C.sub.10 monovalent monocyclic group including at least one selected from N, O, P, and S as a ring-forming atom. Examples thereof include a tetrahydrofuranyl group and a tetrahydrothiophenyl group. As used herein, the term “C.sub.3-C.sub.10 heterocycloalkylene group” refers to a divalent group having the same structure as the C.sub.3-C.sub.10 heterocycloalkyl group.
(260) As used herein, the term “C.sub.3-C.sub.10 cycloalkenyl group” refers to a C.sub.3-C.sub.10 monovalent monocyclic group having at least one double bond in a ring but without aromaticity Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. As used herein, the term “C.sub.3-C.sub.10 cycloalkenylene group” refers to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkenyl group.
(261) As used herein, the term “C.sub.3-C.sub.10 heterocycloalkenyl group” refers to a C.sub.3-C.sub.10 monovalent monocyclic group including at least one selected from N, O, P, and S as a ring-forming atom, and includes at least one double bond in a ring. Examples of the C.sub.3-C.sub.10 heterocycloalkenyl group include a 2,3-hydrofuranyl group, and a 2,3-hydrothiophenyl group. As used herein, the term “C.sub.3-C.sub.10 heterocycloalkenylene group” refers to a divalent group having the same structure as the C.sub.3-C.sub.10 heterocycloalkenyl group.
(262) As used herein, the term “C.sub.6-C.sub.60 aryl group” refers to a C.sub.6-C.sub.60 monovalent group having a carbocyclic aromatic system and the term “C.sub.6-C.sub.60 arylene group” refers to a divalent group having a C.sub.6-C.sub.60 carbocyclic aromatic system. Examples of the C.sub.6-C.sub.60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C.sub.6-C.sub.60 aryl group and the C.sub.6-C.sub.60 arylene group include two or more rings, the two or more rings may be fused to each other.
(263) As used herein, the term “C.sub.2-C.sub.60 heteroaryl group” refers to a monovalent group having a C.sub.2-C.sub.60 carbocyclic aromatic system including at least one heteroatom selected from N, O, P, and S as a ring-forming atom and the term “C.sub.2-C.sub.60 heteroarylene group” refers to a divalent group having a C.sub.2-C.sub.60 carbocyclic aromatic system including at least one heteroatom selected from N, O, P, and S. Examples of the C.sub.2-C.sub.60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C.sub.2-C.sub.60 heteroaryl group and the C.sub.2-C.sub.60 heteroarylene group include two or more rings, the two or more rings may be fused to each other.
(264) As used herein, the term “C.sub.6-C.sub.60 aryloxy group” refers to —OA.sub.102 (wherein, A.sub.102 is the C.sub.6-C.sub.60 aryl group) and the term “C.sub.6-C.sub.60 arythio group” refers to —SA.sub.103 (wherein, A.sub.103 is the C.sub.6-C.sub.60 aryl group).
(265) As used herein, the term “monovalent non-aromatic condensed polycyclic group” refers to a monovalent group having two or more rings that are fused to each other, including only carbon as a ring forming atom, wherein the entire molecule does not have aromacity. Examples of the non-aromatic condensed polycyclic group include a fluorenyl group or the like. As used herein, the term “divalent non-aromatic condensed polycyclic group” may refer to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
(266) As used herein, the term “monovalent non-aromatic hetero-condensed polycyclic group” refers to a monovalent group having two or more rings that are fused to each other, including a heteroatom selected from N, O, P, and S as a ring-forming atom, in addition to carbon, wherein the entire molecule does not have aromaticity. Examples of the monovalent non-aromatic hetero-condensed polycyclic group include a carbazolyl group or the like. As used herein, the term “divalent non-aromatic hetero-condensed polycyclic group” refers to a divalent group having the same structure as the monovalent non-aromatic hetero-condensed polycyclic group.
(267) As used herein, the term “Ph” refers to a phenyl group, the term “Me” refers to a methyl group, the term “Et” refers to an ethyl group, and the term “ter-Bu” or “Bu.sup.t” refer to a tert-butyl group.
(268) Hereinafter, an organic light-emitting device according to an embodiment will be described in detail with reference to Synthesis Examples and Examples. Hereinafter, the expression “A was used instead of B” in the Synthesis Examples refers to the fact that a molar amount of A is the same as a molar amount of B.
(269) The following Examples and Comparative Examples are provided in order to highlight characteristics of one or more embodiments, but it will be understood that the Examples and Comparative Examples are not to be construed as limiting the scope of the embodiments, nor are the Comparative Examples to be construed as being outside the scope of the embodiments. Further, it will be understood that the embodiments are not limited to the particular details described in the Examples and Comparative Examples.
EXAMPLES
Example 1
(270) An ITO glass substrate (available from Corning), on which an ITO layer having a thickness of 15 Ω/cm.sup.2 (1200 Å) was formed, was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonically washed with isopropyl alcohol and pure water for 5 minutes each, irradiated with UV for 30 minutes, exposed to ozone to wash the substrate, which was and then loaded onto a vacuum deposition device.
(271) m-MTDATA was deposited on the ITO anode to form an HIL having a thickness of 600 Å, HT5 was deposited on the HIL to form an HTL having a thickness of 200 Å and then Compound 1A was deposited on the HTL to form an AL having a thickness of 100 Å. AND (host) and FD1 (dopant) were co-deposited on the AL at a weight ratio of 95:5 to form an EML having a thickness of 200 Å.
(272) ET1 was deposited on the EML to form an ETL having a thickness of 300 Å, LiF was deposited on the ETL to form an EIL having a thickness of 10 Å, and then Al was deposited on the EIL to form a cathode having a thickness of 1,000 Å, to thereby manufacture an organic light-emitting device.
Example 2
(273) An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2A was used instead of Compound 1A for forming the AL.
Example 3
(274) An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 4A was used instead of Compound 1A for forming the AL.
Example 4
(275) An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 5A was used instead of Compound 1A for forming the AL and ET17 was used instead of ET1 for forming the ETL.
Example 5
(276) An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 5A was used instead of Compound 1A for forming the AL and ET19 was used instead of ET1 for forming the ETL.
Comparative Example 1
(277) An organic light-emitting device was manufactured in the same manner as in Example 1, except that NPB was used instead of Compound 1A for forming the AL.
Comparative Example 2
(278) An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 1A for forming the AL.
(279) <Compound A>
(280) ##STR00075##
Evaluation Example 1
(281) Driving voltages, current densities, brightness, efficiencies, and half-lives of the organic light-emitting devices manufactured in Examples 1 to 3 and Comparative Examples 1 and 2 were measured by using Kethley SMU 236 and spectrophotometer PR650, and the results obtained therefrom are shown in Table 1 below. In this regard, lifespan is a comparative lifespan based on Example 1.
(282) TABLE-US-00001 TABLE 1 Auxiliary Driving layer ET voltage Efficiency material material [V] [cd/A] Lifespan Example 1 Compound 1A ET1 4.2 1.15 1 Example 2 Compound 2A ET1 4.1 1.2 1.3 Example 3 Compound 4A ET1 4.12 1.1 1.2 Example 4 Compound 5A ET17 4.1 1.1 1.5 Example 5 Compound 5A ET19 4.1 1.1 1.6 Comparative NPB ET1 4.05 0.9 0.8 Example 1 Comparative Compound A ET1 4.12 1 0.9 Example 2
(283) It may be observed from Table 1 that driving voltages, efficiencies, and lifespans of the organic light-emitting devices manufactured in Examples 1 to 5 are better than those of the organic light-emitting devices manufactured in Comparative Examples 1 and 2.
(284) As described above, an organic light-emitting device according to an embodiment may have a low driving voltage, high efficiency, and a long lifespan.
(285) Example embodiments have been disclosed herein, and although specific terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent to one of ordinary skill in the art as of the filing of the present application, features, characteristics, and/or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of skill in the art that various changes in form and details may be made without departing from the spirit and scope thereof as set forth in the following claims.