Organic electroluminescent device
View Patent ↗Provided is an organic electroluminescent device including an organic layer interposed between a pair of electrodes, the organic layer including a layer formed of a titanium oxide derivative or a mixture layer containing a titanium oxide derivative. The organic electroluminescent device has higher luminescent efficiency, a longer lifetime and a lower operating voltage than a conventional organic electroluminescent device, and can be easily manufactured.
1. An organic electroluminescent device, comprising:
a pair of electrodes; and
an organic layer interposed between the pair of electrodes, the organic layer comprising:
at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer; and
a titanium oxide derivative layer consisting of 100% of a titanium oxide derivative represented by Formulae 1 through 4 formed on said at least one layer as a separate layer;
Ti(OR 1 ) 4 (1)
where R 1 is each independently CH 3 CO—CH═CCH 3 —, C 2 H 5 OCO—CH═CCH 3 —, —CH 3 CH—COO − NH4 + , —COR 2 , —CO(C 6 H 4 )COOR 3 , or a C 1 -C 12 alkyl group;
R 2 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
R 3 is a substituted or unsubstituted C 1 -C 12 alkyl group;
where R 4 is a substituted or unsubstituted C 1 -C 12 alkyl group; and R 5 is a substituted or unsubstituted C 1 -C 12 alkyl group;
where R 6 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
where R 7 is a substituted or unsubstituted C 1 -C 12 alkyl group.
2. The organic electroluminescent device of claim 1 , wherein the titanium oxide derivative is selected from the group consisting of tetraisopropyl titanate, tetra-n-butyl titanate, tetrakis(2-ethylhexyl)titanate, acetylacetonate titanate chelate, ethyl acetoacetate titanate chelate, triethanolamine titanate chelate, lactic acid titanate chelate ammonium salt, and a mixture thereof.
3. The organic electroluminescent device of claim 1 , wherein the titanium oxide derivative layer is formed using a solution of 1 wt % to 90 wt % of the titanium oxide derivative dissolved in a solvent selected from the group consisting of alcohols, aromatic groups, dimethyl formamid, acetone, and a mixture thereof.
4. The organic electroluminescent device of claim 1 , wherein the organic layer further comprises at least one layer selected from the group consisting of a hole blocking layer, an electron injection layer, and an electron blocking layer.
5. The organic electroluminescent device of claim 1 , wherein the titanium oxide derivative layer is prepared by using a wet coating method comprising spin coating and a drying process, or by transferring a prepared titanium oxide derivative film using thermal deposition, laser deposition, heat bar, magnetic induction heating, or ultrasonic friction.
6. An organic electroluminescent device, comprising:
a pair of electrodes; and
an organic layer interposed between the pair of electrodes, the organic layer comprising a titanium oxide derivative layer consisting of a titanium oxide derivative represented by Formulae 1 through 4 and an organic material,
Ti(OR 1 ) 4 (1)
where R 1 is each independently CH 3 CO—CH═CCH 3 —, C 2 H 5 OCO—CH═CCH 3 —,—CH 3 CH—COO − NH4 + , —COR 2 , or —CO(C 6 H 4 )COOR 3 ;
R 2 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
R 3 is a substituted or unsubstituted C 1 -C 12 alkyl group;
where R 4 is a substituted or unsubstituted C 1 -C 12 alkyl group; and R 5 is a substituted or unsubstituted C 1 -C 12 alkyl group;
where R 6 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
where R 7 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
the organic material is selected from the group consisting of copper phthalocyanine (CuPc); TCTA, m-MTDATA, IDE406, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), 1,3,5-tricarbazolylbenzene, 4,4′-biscarbazolylbiphenyl, polyvinylcarbazole, m-biscarbazolylbenzene, 4,4′-biscarbazolyl-2,2′-dimethylbiphenyl, 4,4′,4″-tri(N-carbazolyl)triphenylamine, 1,3,5-tri(2-carbazolylphenyl)benzene, 1,3,5-tris(2-carbazolyl-5-methoxyphenyl)benzene, bis(4-carbazolylphenyl)silane, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′diamine (TPD), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl benzidine (α-NPD), N,N′-diphenyl-N,N′-bis(1-naphthyl)-(1,1′-biphenyl)-4,4′-diamine (NPB), IDE320, poly(9,9-dioctylfluorene-co-N-(4-butylphenyl)diphenylamine) (TFB), poly(9,9-dioctylfluorene-co-bis-(4-butylphenyl-bis-N,N-phenyl-1,4-phenylenediamine)) (PFB), DCM1, DCM2, Eu(thenoyltrifluoroacetone) 3 (Eu(TTA) 3 ), dicyanomethylene-2-butyl-6-(1,1,7,7, -tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB), (tris-(8-hydroxyquinolinato)aluminum ( Alq 3 ), rubrene, 4,4′-N-N′-dicarbazole-biphenyl (CBP), bis[2-(2′benzothienyl)-pyridinato -N,C 3 ]iridium (BTPIr), coumarin 6, C545T, quinacridone, Ir(ppy) 3 , C314S, C343S, C7, C7S, C6S, C314T, C545T, C6, green 223, Bis-DAPOXP, Spiro-DPVBi, Spiro-6P, triarylamine compounds, 4,4′-bis(2,2-dinhenylvinyl)-1,1′-bipnhenyl (DPVBi), DSA, Compound(A), bis[2-(4,6-difluorophenyl)pyridinato-N,C 2 ]iridium picolinate (FIrpic), CzTT, anthracene, 1,1,4,4-tetraphenyl-1,3-butadiene (TPB), 3,5,3′, 5′-tetrakis-tert-butyldiphenoquione; 1,2,3,4,5-pentaphenyl-1,3-cyclopentadiene (PPCP), DST, TPA, OXD-4, BBOT, AZM-Zn, BH-013X, IDE140, IDE105, bis(2-methyl-8-quinolato)-(p-phenylphenolato)-aluminum (Balq), bathocuproine (BCP), and tris(N-arylbenzimidazole) (TPBI), BaF 2 , LiF, NaCl, CsF, Li 2 O, BaO; and
TCTA having a chemical structure of:
m-MTDATA having a chemical structure of:
rubrene having a chemical structure of:
Ir(ppy) 3 having a chemical structure of:
C314S having a chemical structure of:
C343S having a chemical structure of:
C7 having a chemical structure of:
C7S having a chemical structure of:
C6S having a chemical structure of:
C314T having a chemical structure of:
C545T having a chemical structure of:
CzTT having a chemical structure of:
Anthracene having a chemical structure of:
DST having a chemical structure of:
TPA having a chemical structure of:
OXD-4 having a chemical structure of:
BBOT having a chemical structure of:
AZM-Zn having a chemical structure of:
Spiro-DPVBi and Compound (A) having chemical structures of:
and a mixture thereof.
7. The organic electroluminescent device of claim 6 , wherein the titanium oxide derivative layer is an electron transport layer.
8. The organic electroluminescent device of claim 6 , wherein the titanium oxide derivative layer is formed using a solution of 1 wt % to 90 wt % of the titanium oxide derivative dissolved in a solvent selected from the group consisting of alcohols, aromatic groups, dimethyl formamid, acetone, and a mixture thereof.
9. The organic electroluminescent device of claim 6 , wherein the titanium oxide derivative is represented by one of Formulae 2, through 4:
where R 4 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
R 5 is a substituted or unsubstituted C 1 -C 12 alkyl group;
where R 6 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
where R 7 is a substituted or unsubstituted C 1 -C 12 alkyl group.
10. The organic electroluminescent device of claim 9 , wherein the titanium oxide derivative is selected from the group consisting of acetylacetonate titanate chelate, ethyl acetoacetate titanate chelate, triethanolamine titanate chelate, lactic acid titanate chelate ammonium salt, and a mixture thereof.
11. The organic electroluminescent device of claim 6 , wherein the titanium oxide derivative layer is an emissive layer.
12. The organic electroluminescent device of claim 11 , wherein the emissive layer has a thickness ranging from 10 nm to 100 nm.
13. The organic electroluminescent device of claim 6 , wherein the organic layer further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emissive layer, and an electron transport layer.
14. The organic electroluminescent device of claim 13 , wherein the organic layer further comprises at least one layer selected from the group consisting of a hole blocking layer, an electron injection layer, and an electron blocking layer.
15. An organic electroluminescent device, comprising:
a pair of electrodes; and
an organic layer interposed between the pair of electrodes;
a titanium oxide derivative layer consisting of 100% of a titanium oxide derivative represented by Formulae 1 through 4
Ti(OR 1 ) 4 (1)
where R 1 is each independently CH 3 CO—CH═CCH 3 —, C 2 H 5 OCO—CH═CCH 3 —, —CH 3 CH—COO − NH4 + , —COR 2 , or —CO(C 6 H 4 )COOR 3 or a C 1 -C 12 alkyl group;
R 2 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
R 3 is a substituted or unsubstituted C 1 -C 12 alkyl group;
where R 4 is a substituted or unsubstituted C 1 -C 12 alkyl group; and R 5 is a substituted or unsubstituted C 1 -C 12 alkyl group;
where R 6 is a substituted or unsubstituted C 1 -C 12 alkyl group; and
where R 7 is a substituted or unsubstituted C 1 -C 12 alkyl group.
16. The organic electroluminescent device of claim 15 , wherein the organic layer comprises:
at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer; and
the titanium oxide derivative layer formed on said one layer.
17. The organic electroluminescent device of claim 15 , wherein the titanium oxide derivative is selected from the group consisting of tetraisopropyl titanate, tetra-n-butyl titanate, tetrakis(2-ethylhexyl)titanate, acetylacetonate titanate chelate, ethyl acetoacetate titanate chelate, triethanolamine titanate chelate, lactic acid titanate chelate ammonium salt, and a mixture thereof.
18. The organic electroluminescent device of claim 15 , wherein the titanium oxide derivative layer is formed using a solution of 1 wt % to 90 wt % of the titanium oxide derivative dissolved in a solvent selected from the group consisting of alcohols, aromatic groups, dimethyl formamid, acetone, and a mixture thereof.